I have a separate short term rental insurance policy (insurance agent recommended short term policy over long term since it's ultimately being used as a short term rental) Curious if that is the same as the Airbnb $1M liability insurance or if they have a separate one

Separately, the benefits and disadvantages of renting to Section 8 is a topic of extended debate on this forum.

One workaround could be keeping a separate spreadsheet to track your adjusted tax basis accurately and only using Stessa for operational insights.You could also reach out to a cpa and see if they have a specific recommendation for software to use.  

I just used my attorney as our registered agent, PO Box as our business address, and a separate LLC as the holding company. $50/ LLC and it literally takes less than 20 minutes for each LLC and costs less than $20/ yr. to renew each LLC.

You can simply request a separate check for the $100 increase to bring the total deposit in line with the new rent amount.

However, could she gift half the property to the son who lives with her, which would allow them each to use their own separate $250k capital gain exclusion? 

Question 2: Is it a good idea to put every piece of property into a separate LLC entity (1 for 1) or is it okay to put a few properties into the same LLC?

Two separate property appraisers (at the direction of the lender) were sent out to appraise, and neither was willing to appraise it as a "residence", and thus financing fell through (conventional primary loan).

It’s one thing to learn, but turning knowledge into action—mistakes and all—is what separates those who dream from those who achieve.Let’s keep building and growing!

I'd have to see your overall layouts but I think you are on the right track. we build 3 story stacked triplexes and it's very efficient so don't be afraid to go up either. anytime you build more than 1 structure costs are much higher but if its just to offset mortgage and you want to be separate then I understand.