We do have a mortgage, so we would need to talk with our lender to avoid the "due on sale" clause (at least that's how it has been explained to me).

I also see your point about avoiding bargain basement properties, especially insofar as tax shielding is easier with an asset of a reasonable size.Your point about barriers to entry is also interesting, since I suppose those barriers can be geography (natural boundaries of mountains/water), but you're probably referring to that which impedes future construction?

As mentioned elsewhere, as much as you're able to do so now, handle all estate matters so you can avoid probate.

I have been avoiding this forum for so long because well, I am ashamed of myself a little lol.

Then you can avoid the self promotion issue. 

North side: Avondale, west logan square, albany park, rogers parkSouth side: Bronzeville, brighton park, mckinley park, bridgeport, west half of pilsenI agree with “trend is your friend” and avoid areas that might but havnt popped off.

Consider the "2 of the last 5 year rule" to avoid capital gains. 

To avoid scammers and fraudulent paystubs, I contact the applicants place of employment directly to verify that the paystubs are accurate, the company is legitimate, and the duration of the applicants employment.Why do you need TWO YTD paystubs?

I would avoid an above ground pool. 

If you are using RE investing to try to avoid going to school, your intentions are not in the correct place.