I don't like the short timelines/constraints of 1031 exchanges though. 

Short Term: No, not happening. 

I reached out to Ward Hanigan but that short course does not look available currently.

The only exception might be if you plan to and if your market supports short term rentals.

As MFH is dropping there shorts to get and keep full occupancy, offering every spif imaginable, larger units are to accommodate families of size or multi-gen living is a rare inventory. 

The property that I have, my family owns is not currently an Airbnb or a short term rental.  

Which based on the gnashing of (mostly “frugal” REI) teeth, was the lowest in the industry (for most of you, especially with multiple, active accounts).I have my IRA, HSA, and CESA accounts (more on Solo’s shortly) with Quest.

I'm trying to analyze my first property and not sure how to set it up to run the number using the calculator tools here. 2 of the units are successful Airbnb short term rentals, and the other two units are month to month rentals to existing tenants.

., short-term rental, mid-term rental)?

From what I’ve read in The Economist, short-term construction loans or hard money financing could be a great fit to cover the $90K needed.