The 1031 can defer capital gains taxes, but it’s crucial to identify a like-kind property and complete the exchange within the IRS timelines.

This is just for practice for now so the most important thing is just looking at the numbers to gain an understanding, don't put too much pressure on it at this point, it's a muscle you have to build by doing reps. 2.

But I’d like to get a gain from this, specifically some monthly income for myself.

Starting local in Pittsburgh is wise, and as you gain experience, consider expanding your reach.

It's all about your time horizon and if you are more focused on immediate gains, or long term appreciation. 

The S Corp treats each property as inventory (think retail) and it works out to save me on short term gains. 

Have you investigated full roof replacement to seal it completely and gain a warranty on the roof for a few years to eliminate leak concerns? 

I have an unplanned capital gain over several decades due to a property interest I inherited.

I would do these to current code standards, and other smaller alterations all to code, without gaining permits.

Gained capital via the assorted down payments.