If this is your dream retirement place, perhaps you use the LTR to simply subsidize your purchase even if it's not fully cash-flow positive. 

Now that I am retired, I am eager to: 1) Gain hands-on experience in flipping homes in Florida, 2) Find properties with potential for value-add/forced appreciation, 3) Partner with experienced home flippers for collaborative projects.

Assuming you have ANY other funds to invest instead, what’s the upside to using your retirement funds instead?

I recently had a landlord at a workshop who owned and managed a portfolio of low end properties for over 30 years, he is basically broke and can't retire.

But they are also looking for clients for life IE they want all your banking all your CC if you use those things.. your retirements accounts etc etc..

With house hacking, I feel like you only need a few properties to be able to build cash flow and set yourself up for retirement.

I met guys who were “reservist” but just kept extended AD orders and were retiring soon.

I find it more rare for people retired with money to go all in with a DST and give up full control like that.

My realtor retired from Banking Management about 30 years ago.

I am retired military and have used the VA for myself and helped others also use it on their real estate journey in the area.