Sounds like you’re in a strong financial position, and it’s clear you’ve put a lot of thought into your strategy. 

I have helped dozens of BP members purchase and sell STR homes near Disney.

That's not a great strategy for Danbury.

Include an exit strategy, tax planning, and insurance to protect both parties.

If they tell you no, then stop and find a different strategy.

We've done about a dozen flips.

Thanks @Robin Simon I plan on reproducing this strategy in 2025 to buy 3-5 more. 

Based on the numbers and my strategy, do you think this is a good investment for my first property?

I'll happily pay the commission and his GC fees, and we'll hopefully do this a few dozen times over the coming years.My general question is: how are other people handling this awkwardness?

Fortunately for our 100+ house community, the fire department was already on site battling the brush fire and about a dozen fire fighters frantically extinguished the 4 or 5 roofs burning.This is insignificant compared to what has happened in LA, Palisades, Malibu and Altadena however having lived through Hurricane Andrew and many other major storms even this experience was drastically more terrifying and chaotic.