Watching and playing an active role in the transition from primarily 2nd liens to 1st and 2nd liens, laid the foundation for me partnering with GSP REI.

You're not in the position to be a cash buyer...as a former wealth manager, it's simply not a good play for you for many of the reasons stated above and more.  

You need to remember that, hopefully, this is a long-term play for you, so work with a trusted STR designer (I have great recommendations), and spend the money upfront so you can be the most successful in your area.

My fiance and I are in a unique situation as I play baseball professionally, and she works online and plans to live with me during my season.

Potential redevelopment or ADU play. 

Working with a great broker can also help as they will know how best to represent your interests and play the game.

I also think, the flat rate ppl are playing to a race to the bottom. 

Umbrella insurance will never come into play for Property damage (fires, storms, floods, etc.)It is liability coverage only.I'm an insurance agent and have seen umbrella claims from fatal car and boat accidents. 

How will it all play out? 

Income-based valuation only comes into to play once you get into commercial property (5 units and up).