We travel for work (healthcare) and chronically live out of MTRs, so it will be our first time operating a shorter term, but won’t be an entirely foreign situation to us.

*As a side note, I think maybe it would be fun also to try and identify where new technology or machine-learning driven approaches could increase efficiency in the spaceAs for my financial situation, personally, I have around 50k saved but 20k of it is tied up in assets I don't want to pay capital gains tax on.

In my own situation, we went a long time without insurance.  

That's what I would do in your situation.

Complicated post and I realize this might be more geared to a CPA, but figured I would try here and see if anyone else has come across a similar situation.

They just plug you into the conveyor belt of webinars and canned training that doesn't take them any time to create, but also isn't tailored to your specific situation. 

In similar situations @Nick Am, keep us updated on your findings.

Changes to local landlord/tenant laws and new situations involving tenants lead to these annual updates.

The unique format of this event, which consists of high-level education, gamified networking, mastermind breakout sessions, case studies, group deal analysis, market deep dives, and peer-to-peer coaching facilitation makes this the most impactful local real estate investor group a real estate investor can be a part of.The foundation of the group is built around the belief that everyone in the room has the potential to change the world… however most of us never have the time, energy or financial situation to even dare to dream big enough.

I think the ultimate situation for what I described above (not the plan, but a possible outcome) could look like this:Rent main house by the rooms while constructing ADU.