You would have depreciation recapture on the items you depreciated (75k), taxed at ordinary income rates and then any of the actual property appreciation would be taxed at favorable capital gains rates (50k). 1031 exchange will allow you to defer all of that gain as long as you meet conditions.

It seems like it could work great in this scenario as long as the numbers work.  

But as long as it's at least 2 out of the past 5 you get the whole enchilada.

It could be any side-hustle you want just as long as you like it and your able to save some extra $$$.2.

You can average the amounts or use the higher $29,000 figure if it reflects market conditions, as long as you document your methodology and provide evidence, such as sales data or an appraisal.

currenty I just fund land flippers so we are in and out of the deals before we even pay prop tax's so I dont really care what they are as long as we sell for a profit ( which we do) its all good.

WAIT as long as you can and don't die.This is easier said than done but it's a proven model to create wealth in your life that has worked for many people over time.I just borrow the down payment as a loan or equity in the property.

If we see too much or see anything that looks suspicious we'll ask about it and maybe disqualify someone as long as we're adhering to fair housing and HUD guidelines, but that's not usually something that comes up. 

As long as you and your CPA maintain thorough and accurate records, you should be in good shape.

As long as it's approved for STR use then I would go this route.1) Buy nice once and never buy again.