I appreciate all the input on this hypothetical. @ Stan, I look at a property like this the same way I'd look at a penny stock. It's cheap for a reason but under the right circumstances it could be a money maker or, alternatively, it could be a value trap. If I buy a thousand shares of XYZ trading at $2, hey if it runs up to $3 then I just made $500 bucks. If it delists and goes belly up then hey I'm out $2 grand, oh well.
If it were a security I'd trade it on paper for a while to see how it behaves but I'm not sure that's as easy to do with a hard asset.
I'm looking for a slow pitch to start off with, something that considering the worst possible scenario, if everything possible goes wrong, I can still come out of the game okay.
When I started trading securities I started off with utilities, GE, steady eddie blue chips, issues that aren't going to hurt you barring the apocalypse. Then I started trading pennies in small positions just to get a feel for momentum and volume. That helped teach me about entry and exit strategies, creating a thesis for every trade. These trading strategies then helped me formulate my investment philosophy for long-term holdings (i.e., finding value in undervalued issues that return capital to shareholders).
I don't want to buy a property, have to dump a bunch of money in into it and then it becomes an albatross around my neck. I'm a value investor. I like margins of safety and I like cheap, as in on sale, not cheap as in worthless.
I appreciate your words of wisdom and the points you make. Very good stuff.