For me it's been a mixture of grinding (started off on Like The Wind Indy, then progressed onto American Car Indy) and trying to be astute in the UCD.
Because I only intend to trade cars that I don't want, I've taken to buying certain cars more than once with the idea of trading them in the future. Cars that I think are either rare or in demand - but it's taken a little while to get used to the market and figure out what people really want.
I picked up a Fireblade quite early on, and then another a bit later, figuring not many people might have it. It seems that's not really the case, but luckily I managed to trade it for something I wanted, although I can't remember what.
M3 GTRs seem to appear all the time in my UCD, but seem to be in demand in the marketplace, so I buy them quite often. I think I have 3 at the minute, and had to stop myself blowing another 300K on another 'just in case'. I get a lot of M3 CSLs as well, which are cheaper, and not as desirable, but people out there are still looking for them. RUF Yellowbirds seem to go down quite well, and in fact all RUFs seem to be fairly tradeable, Impreza 22Bs are in high demand, it seems like people are after Supra RZs, although nobody has made an offer on mine yet.
On a few occasions I've traded up pretty successfully, getting a car that I really want that is of a higher value than what I'm offering. Sure, perhaps it's a dupe from the other person, otherwise it's unlikely that they would trade for something of lesser value, but having said that I swapped a M3 GTR (costing about 300K) for a RUF BTR (about 100K) because I wanted it and figured it might not come up in my UCD. (It did, and now I have two, so hopefully somebody else out there will want my BTR for a car that is more expensive). The craziest (well, to me at least) is when somebody swapped me their car for my paint, but each to their own I guess.
On other occasions I've bought crap, such as the Beetle RSi, which *nobody* wanted, so now I tend to test the water if it's something I'm unsure about, seeing if there's any interest out there before I go and blow my hard-earned cash on a lemon.
It's probably not the quickest way to success, and given the amount of times I've grinded on different Indy races I probably could have afforded some of these 4M cars by now, but I pretty much check the UCD between every race and too often there's something in there that I want, so . . .
Purists probably think it's no better than duping, but I'm fairly happy with the arrangement I've got, and it's allowed me to trade up for a Ferrari P4 and Chaparral 2D (and hopefully a GT40 '69) which I would otherwise stand little chance of ever getting around to actually affording, and other nice little motors such as an RS200 Rally Car, Pajero Rally Raid, Lotus Carlton etc. In the meantime this has allowed me to also earn enough cash to buy a few 1M/1.5M cars as well as plenty of 200K-800K cars that are bringing the collection on nicely.
Sure, I haven't got 1 FGT or X1 or X2010 or whatever it is that these people seem to have limitless supplies of, but I'm really not that bothered to be honest, I've got lots of nice cars and I'm happy.
Works for me anyhoo