Setup and quirk
Raymond starts the game at Jack's Diner, in the blue district. This is a very good position because it is quite central, plus Raymond has a fast car. Additionally, he starts the game with a dropship pass, so his mobility is very good.
He places a physical lead at A+ Athletic Club and a document lead at The Root. Those two are obviously in range from the starting position, and even in range of each other, so he may follow these leads and still have time remaining for drawing cards, for instance.
The testimony leads are a bit harder to come by. The Levy University and the Starlight Crusade are both ritzy locations, which are risky for Raymond. So if Noise isn't near and there's nobody at Monroe & Associates you'll have to wait until some of them are followed if you want to follow a testimony lead, or enter dangerous places, or go meet them after a few moves. He isn't especially helped by any of the cases, either.
Raymond's quirk is his memories. On the good side, this is what gives Raymond his increased hand size, and the ability to draw two cards for one time every turn (the equivalent to an extra action for drawing). But there's also a bad side for it. Raymond can't let go his old mistakes out of his mind, and your opponents will get one card with which they can mess with him.
They are basically easy to avoid, but you have to take them into account. Never draw to seven cards, at least if you have some favors you want to use. Don't touch the Beanstalk at all (The Root is OK, and The Midway if you wish (though it is usually a waste of time) but no further! You shouldn't go to the moon, and if you do, be very careful of not getting into any fight there (which is hard to avoid), and of course, have a dropship pass ready for the return trip.
This leaves only one memory whose trigger (starting your turn on Earth) you can't really avoid (you could hide in The Root after each turn, but then you're hurting yourself, so embrace that memory, because it's going to hit you). This memory will move you to a nighlife location (thankfully enough, on Earth) and make you lose 3 Time. You're likely to then lose the rest of your turn to a dark card, so you may want to hold on your counter card, or just accept that you're going to lose that turn.
Raymond's plots are special in that they take six days to resolve each step. This means you'll only see one of his plots, and you have to be extra careful because if it goes south, you'll get a costly amount of negative victory points. Since Raymond only has two plots, there's no double keyword plot. Many of your plot parts are vulnerable to actions taken by other players after your turn is over, so you should be careful about baggage.
Haunted by the Past: This plot is about Raymond's friend getting killed in the war because Raymond left his position to go after Kate, and how much it hurts Raymond to remember that. The keywords are Insight and Regret, though there's not much difference in the plots' keywords. A couple of cards are a bit tougher with this plot since they specifically mention Regret.
If you get this plot, do all that is in your hands in order to get into the good crossroad, because this will make Parsons found, which enables a couple of your light cards and stops a few dark cards. Furthermore, once you get into the good crossroad, a happy ending is guaranteed. In order to do that, you get good baggage by sacrificing evidence, and bad baggage when an opponent plays one of your Haunted (not Haunted by the Past) cards. If you get into the desired good crossroad, good baggage will come with every light card drawn after the first two cards of each turn. Bad baggage comes with an opponent drawing and revealing a dark Haunted by the Past card. If however, the plot goes into the bad crossroad, now Raymond gets good baggage for each different nighlife location he enters on his turn (and those cause a complete dark shift now). This causes you to expose yourself to dark cards, but in order to give you bad baggage, they have to sacrifice two of your dark cards, so that causes some tension. A good route is Nat's Microbrewery - The Speakeasy (for 1 time) and then from any of those two, stop at A+ Athletic Club and drop by Pat O'Shea's Pub. If the crossroad (any) resolves positively, Keene will become peaceful (no game effect, though).
Old Flame: This plot is about Kate, Raymond's old love affair, who is back in town. Kate always means trouble. If you get this plot, forget about finding Parsons, which means there'll be two light cards you won't be able to play. The keywords on this one are Focus and Denial. The happy endings on this one will let you exchange your Kate favors for two normal favors of your choice at the end of the game (obviously, the ones that got more links). The worst result will make you lose your Kate favors and give you one trauma for each one. The lesser sad ending eliminates Kate (again making you lose your favors), but gives you a bonus victory point to your conspiracy tokens.
The start of this plot makes you sacrifice 2 time in order to get one good baggage, which is always a hard thing to do, and will get bad baggage by opponents sacrificing two dark cards (don't have to be Raymond's) or one favor. If you manage to get into the good crossroad, you'll get good baggage for each piece of the conspiracy that Raymond uncovers, and bad baggage when a dark card matching this plot is sacrificed. The bad crossroad will give you good baggage each time you play a light card, and bad baggage each time a dark card is played on Raymond.
Raymond's light cards can be split into several groups.
Leads: Flint is a lead following machine. In addition to his fast car, he has several light cards that help him with that. There are a couple cards that let you move leads around (without that pesky "out of my district" rule), another one lets you follow a lead for no time, and another one lets you follow a lead in a location Raymond can reach in one time (without moving there, which also saves time. It's a very important one because you can follow a lead in a dangerous place like a ritzy or nighlife location without triggering the usual plethora of dark cards). You can even cancel the following of a lead by another player to follow it yourself. Finally, you can get double evidence from one lead, or call "dibs" on any lead on the board. As you can see, there's a big flexibility with the leads.
Conspiracy: As a tie-in to the previous group, a few of the cards also help with the conspiracy puzzle, which can be dominated if the other players aren't watching closely. One that can catch everyone by surprise lets you rotate an already placed piece when you're uncovering another piece. This can be used to trick the other players into thinking that a certain something (specific type of favor, for instance) will be valuable and then drop that value late in the game, or in reverse, but harder to manage, raise the value of something your opponents didn't care to hoard. It can also be used sometimes to play on that corner that was unplayable because no lines extended into it, and will now give you two conspiracy tokens. You can also "dig deeper" by free, that is, without having to follow a lead specifically for that reason, which gives easier access to the higher stacks, or you can get a two for one deal in uncovering.
Favors: This one is a weak group. The best card in this group, giving you one of each type of favor, requires Parsons to be found, which is outright impossible in half of the games, and have to wait until the second week at best in the other half. Also, favors are very fragile for Raymond, and they can be easily lost to dark cards or memories. A couple of cards in this group give you kate favors. Kate favors are a very sharp double edged sword, so be very careful with them and try to get them and immediately spend them without moving, and this will remove most of the sting of them, or you can gather them with your last actions of the game if the right groups in the puzzle are connected, or if you're headed to a happy ending of the Old Flame plot.
Mobility: You have one card that lets you move anywhere on the board. Good for crossing the board if you got moved to a far away place, or a limited time offer appears at the other side of the boards. Another one gets you a dropship pass, which is the same thing one step removed. With these and your starting pass, you can't be far away from the action for long. If you really need to get something done in the moon, you can use these cards for a "come and go" trip, but it better be worth the risk of stepping on the moon and the cost in light cards or dropship passes. Again, avoid the Beanstalk like the plague (the plague would be more pleasant). I'm adding a card that gives you three extra time in this group, on the basis that more time lets you reach further away. Don't be too excited, you have to find Parsons first. If you do, however, this is a great card.
Defense: This is the last group, formed by a couple cards. You have a card that lets you cancel a dark card played on you, but the big one makes your opponents discard all of Raymond's dark cards, which means you can have a day free of risks, letting you get into ritzy and nighlife locations without fearing the worst. Be aware that Flint's Memories are still out there, so the Beanstalk is still out of bounds if you were thinking on using this card to go to the moon.
Of course, not everything will go right for you. Raymond, like everyone, has to be aware of his weaknesses dictated by his dark cards.
There are several cards with the Haunted keyword, of varying levels of nastiness. One of your dark cards (whose trigger is unavoidable, since you're bound to start your turns) will make Haunted cards cost 0 shift that turn, so if that is played (and not cancelled) you have to be extra careful. Use your Kate favors immediately if possible. If you don't have any, this card isn't so dangerous. Haunted cards also hinder you when you're trying to find Parsons.
In the start of turn group you have some nasty ones, especially if Parsons is missing. Things like losing 3 time, or preventing you from following any leads this turn. Also, one dark card (and this one doesn't care about Parsons) will make you lose all favors of one type, so don't hoard them or have your cancelling card ready. Sadly, this cancelling card is overworked, it seems.
Fortunately, Raymond doesn't have cards that say "play when Raymond enters any location" without any additional conditions, with one exception that will move you to Old War Memorial. You can get into a fight there if someone plays a card, but they're not too big (not small, either). However, there are several places that will give you trouble. Avoid ritzy locations, or you risk having that action cancelled (the lesser evil), or losing several favors. Avoid nighlife locations if you don't want to end your turn (it's OK as the last action of your turn, especially if you can afford getting one bad baggage). Don't move around if you have any Kate favors with you, or you may lose three time, or three light cards, or one favor (again, the lesser evil).
Be a bit wary of seedy locations because you can get into fights there, though they're not crippling. But if you can find an alternative route of normal locations, that's better. Again, no big trouble late in your turn (as your last action), especially with the Old Flame plot. There are a few cards that trigger off other actions (gaining a Kate favor, placing evidence, or using a major location), but they are minor inconveniences.
Raymond has a nice time with leads and the conspiracy puzzle. Take any chance of completing a five in a row in the puzzle, and of course try to get your guilty hunch correct, which is not too hard to do with all your increased following leads abilities (but don't assume). If you can link Cardinal Reese, that's a good thing to do because you can only get one sad ending, and if you have found Parsons, a happy ending is guaranteed, so you don't lose anything from connections with Reese. The other groups are situational. If you have the Old Flame plot resolve positively and you have Kate favors you get to exchange them for two favors of your choice, so you can take advantage of a late connection, where other players haven't had time to gather those favors. If you draw the Jinteki or Haas-Bioroid piece, try to cut them off from the conspiracy, since those being ritzy locations, you aren't likely to have any of their tokens (especially Haas-Bioroid, which is on the moon). If you play conservatively going on normal "daylife" locations, avoiding the Beanstalk and anything above, not filling your hand with cards and not getting Kate favors until the last moment, you shouldn't have too much trouble. Since you can't usually get many points from the conspiracy because of the fragility of your favors, work hard on your plot and the murder.