If everything goes to plan, we will have our vacation home and first STR up and running by the end of May.

As a frame of reference, my property is 2300 sqft, mountain views, 2021 new construction, 4bed/4bath Since you're planning on using the property 95% as a short term rental I'd confirm there isn't a limit on how many days it can be rented versus used by your family when written that way.  

My plan is to take the $800,000 equity I now have in my two unit building, wait until rates drop in the future and borrow against it to purchase a few other properties.

I plan on living in it for at least the first year to qualify for FHA, so it would be in Colorado Springs where I live and work currently.

Once there a plan developed .

I'm planning to start renting out my primary residence and would like to quitclaim transfer the deed into an LLC (just me and my wife).

I am considering pivoting to interest only loans with a refi plan.

We are having a difficult time finding a property manager in the area so we are trying to work on a contingency plan should we have to manage it from afar. 

Just be honest and tell her you are planning on selling and want the home vacant, so she needs to move. 

I'm now planning on growing via small hotel/motel projects and overlooked  non-hospitality commercial.