Very good points all around.
At least at this point in time it's going to be hard selling a '165 for top dollar. While there's a lot of classic car people who believe the next generation of classic collectable cars will be Japanese sport compacts of the '70s-'90s(and I tend to believe that as there's already a market for cars like the first-gen Celicas), that time really hasn't arrived yet for the ST165. It's very much a niche market, at least right now. The situation might be quite different in the next five to ten years.
Personally I'd be willing to pay about $5-7K for a more or less good condition, turn-key '165 with no to minor issues. Is that realistic? However, part of that is because there's a lot of attachment and nostalgia for the platform as my first car was a '162. There's a lot of folks who might want one as a way to score a rare AWD turbo car on cheap, and would be willing to go for a DSM, Galant VR4, or perhaps a fixer-upper WRX instead. Even here, there are people who would likely pick up a '165 if the price is right but would rather have a '185. I'm not saying there isn't a fanbase for '165s, but I don't think there's too many of us around.
However, at the bottom of things I'm not seeing very many clean '165s or at least not many for sale at this point in time. I admit this is a bit discouraging as I'm going to be in the market for a good one(read: not someone else's project as I made that same mistake years ago) in a few months. Any advice for those approaching this from the other end; the ones who have both the money and an enthusiasm for these cars?