Becoming a snowbird by 40 yrs old using VA loans

[Clay Snider]

Quick background, wife and I are both military veterans that bought a duplex, 2 SFH, and a primary residence since late 2016. We just sold all the rentals and paid off our primary home making us debt free. We now have 2 VA loans burning a hole in our pocket again and want to use them to get the hell out of Michigan in the winter and snowbird down in southern Florida.

We can use the VA loans on up to a 4 unit at $981,700. So the plan would be to close on a STR quadplex November/December 2021, move down there for 6 months and establish residency (have to for the VA loan) and turn my primary in Michigan into either a second or investment property. Then in 2022 we will rinse and repeat the same strategy.

I'm looking for someone to poke holes in my broad plan here. What questions should I be asking and what am I missing? I'm completely new to the world of STR's. Thanks in advance!

[Luke Carl]

I want to know more about the Snowbird part of the equation. If you like Florida just move there. No reason to be stuck on the part time idea. Life is short. 

The hardest part of life is figuring out what you want. You want out of Michigan. Just go. Family is over rated. We can be neighbors. Sometimes.