So, in your considerations, I would park right there for a bit and determine how this would look for you.Since you have about 2.5 years to think about it before you would need to spring into action to take advantage of the rollover for tax advantages, maybe you try on a rental and see how it fits. 

He owns 1031 Federal Exchange and is also a tax attorney. 

You could structure the deal as an installment sale or a lease option so the property owner doesn't see a large capital gain tax payment for the sale.And good on you for helping out!

I did not see taxes taken out for profits.

you'll probably still need something long term like software as others have suggested but this was a thought i had... you could see the actual profit or loss from a tax perspective for each property.

These logs regularly end up in the Tax Court and are usually destroyed upon review.

The use of the accelerated depreciation strategy helps real estate investors to reduce the tax liability immediately which therefore increases their bottom line due to the offsetting of income.

Your actual property taxes alone on that will be over $10K a year in 2025 and don't forget about that supplement tax headed your way.I would suggest keeping the others and maybe changing to LTR if that will give you consistent cash flows.  

Tax implications?

I guess I could do some work-arounds -- maybe reserve one unit in the first purchase for use as an AirBnb, and reserve my own time in it when needed - instead of claiming it as a primary.Are either of you (or anyone) familiar with a finance product/loan that will allow me to purchase under $150,000 (w/ strong credit) and do much of my own work and live-in a portion as a primary residence?