and seeking some wisdom for a rookie.Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.Other than reading for my life, how can I number crunch and prepare for this?

Airbnb makes it too easy and I enjoy meeting the people.The trick is to develop a process and stick to it. 

If you're going to own what is effectively a vacation home that is shared with guests that enjoy the outdoors, the Oregon Coast offers a little bit of everything from surfing, golfing, fishing, hiking and investing..The bull's eye for STR investment in general is shrinking and constantly moving.

Putting aside the issue of whether the property continues to appreciate or levels out at the ~170k which we cannot judge, if you actually do the numbers, it will not work out to where a sale is a better option than continuing to enjoy the cash flow, reinvesting those funds in further upgrades or further investment.

Other than that, I want to stay out of their lives and let them enjoy the home they are paying for.

I personally enjoy a misting fan on my patio.Here are some data points below: prices are steady and rates as well; not too much change in the market this far.

If you enjoy it (and the area) it’s likely others will also..so you’re on the right path. 

I appreciate the comment, I always enjoy hearing from another RE attorney. 

I'm particularly interested in multi-family rental opportunities.Outside of real estate, I enjoy fitness and traveling!

So transferring properties with existing mortgages into an LLC without selling them to the LLC is a common strategy for most real estate investors seeking to protect personal assets and possibly enjoy certain tax benefits.