Just make sure you are saving towards those slow months during the peak months, buy a deal at the right price (don't overpay just because its a turnkey STR or you think it will make more money than projected), and look into ways to increase bookings during those slow months with some marketing and operation tweaks. 

I recently sold one I had on Seabrook Island because the club/regime/HOA were frequently changing the rules and making it harder to operate smoothly.

For us STR hosts, I know we are very conscientious about guest experience and I want to be proactive about doing things to ensure my business operates successfully.Thanks!

They'll probably also want to be sure that you are competent to operate the property afterward, because their reputation is tied up in who they do business with, and it's bad for everyone if the property becomes devalued.

@Daniel Cacho I’m 35 years old, have been in the game for over a decade, own 26 doors, run a property management company with 350+ units, and operate a realty brokerage with a small team of agents.

I think it's great to have it in black and white on a spreadsheet and to have an operating timeline.

is it enough to carry you into your next projects while maintaining enough access to keep your current real estate operating smoothly?

I get into contract in my operating company and then assign the contract to the new LLC prior to closing.  

Do you have a track record of purchasing and operating real estate on your own?

The "easy" answer - short term rentals where your brother participates materially in the operations - this would mean 500+ hours a year.It sounds simple from a tax planning perspective.