Think whether this ADU makes sense financially for you, and should you also get tax benefits, then it's a nice bonus.

Having a tenant in the property is not that much of a bonus.

Access to an STR isn't essential, but helpful and bonus when it's personal usage time..- Insurability & Operations costs: Can be considerably lower (especially in comparison to CA) with most coastal regions there is much lower wildfire risk and the properties that are in flood zones, have surprisingly accessible and affordable policy costs.

A bonus for me was is that Nevada is close to all my family still in CA. 

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?

Purchase price: $1,000,000 Cash invested: $400,000 Purchased 25 acres with 30,000 sq ft of buildings with intention of transforming it into a retreat venue - currently leased.

Find yourself a good local housekeeper, treat them well with the occasional bonus and they will be your eyes and ears. 

Approaching the end of my first BRRRR (rehab to be done in 2 weeks) and I'd like to reward my contractor with a cash bonus; I'm wondering what an appropriate amount of money is to give him.

Most homes that I have seen which use a less open floor plan tended to be very expensive ones where real entertaining of clients and the like was a consideration, and curiously those people tended to have formal dining areas where you could not see the kitchen sink… this is why we put bonus rooms in our open concept floor plans. 

Half the crew are driving company vehicles and receiving bonuses on top.