It took me several tries and many CTDs but I have finally managed on Investor/Medium. At first I though you went crazy thinking that such a big amount of passengers and goods can be transported in such a short time but since it is in late game with powerfull and fast engines, it could be done). I have also started few times until I got good starting position (Indianapolis)
Battle plan:
1) Get some money making local routes, preferably near Chicago and Indianapolis, stimulate growth of both cities to ensure they generate enough passengers (hook up food).
2) Hook up passenger transport from Chicago and Indianapolis first because there is only one source. Beer, Footballs and Food could wait a little because I can hook up multiple sources. I have ended up buying some industry closer to Miami too.
3) Once the money stop being a problem, double the tracks to allow for two trains on the same dedicated line, by this time, cities should generate enough passangers for two trains to be fully loaded. Make sure that all cities have Terminals to speed up loading/unloading. Especially busy Miami.
Map worked fine at the beginning, but when I got to 2004, it CTDed on me. I tried to load save from 2003 but it must have already been corrupted because it run to the same time and then crashed again and again. Went to 1995 saved game and just run it fast forward to see if it will finish or crash. It also crashed around 2005. Decided to try avoid the crash by scrapping trains as soon as condition was met (scrap all trains from/to Indianapolis once the Colts fans are all there, scrap all trains from Chicago once the Bears fans are there and so on). This actually worked and I could finish the game. I believe that with better planning and hooking up more resources, it could have been completed by 2002. It really sucks that game is so unstable

I have actually complicated my game by accident by having ultra expensive tunnels (see my post in Roundtrip in the mountains: Test Case (mountains, no bridges) topic) so I ended up building no tunnels at all.