I don't have the rules in front of me, but there seems to be a serious mistake:
I want to make certain I understand the rules regarding insolvency correctly:
-The 'payment' for a run = the 'large city' run number + insolvency amount
So, if an 8+4 runs for 250 ('8' run) + 40 + (11 * 20) = 510 total on its first run after being insolvent;
You don't get the $290 for the normal run. You only get the insolvency amount. It is supposed to be less than the normal income; in fact, there is an optional rule (that is supposed to be used after the players are familar with the earning calculation), that sets the income of an insolvent company to half of the regular income.
Could the '8' skip whistle stops
Whistle stops can always be ignored. Small stations (towns) can't.