I’ll eventually want to transition it into a real thing, but towards the direction of short-term and midterm rental.

I had to generate 100's of leads in order to eventually find a good property that will work.Figure out a process/system that will allow you to generate leads like a machine.

From what you said, you can leave it and then do it in pieces if you aren't going for a full-on upgrade which you shouldn't go overboard on a unit that you will eventually leave and rent out.

It also includes a small commercial space <1200ft which I also hope to rent eventually (it's a conditional permit only for a small business, no retail). 

Hopefully, in a couple of years, they'll be rebuilding and who knows maybe it'll eventually be the place to be.

Or if you just don’t want a job ever you’ll need to find seller financed properties and use your $50,000 as reserves or for light rehabs until you can roll them into DSCR loans eventually and get some cash back out through refinancing them to do the next deal because eventually the $50,000 is going to not be enough.

@Kay Nemen - get comfortable with the idea that rents must increase and must outpace inflation or your returns will eventually degrade to the point where you are loosing money.

I was looking to BRRRR properties, eventually financing them into my LLC.

Pricing is still relatively low for a beach market, and I have several clients who have decided to buy now and rent out their properties with the aim of eventually occupying them when they retire. 

Interest rates are just one factor in the equation.You can offset high (er) interest rates by buying lower priced properties or fixers, or putting down more cash, or having a desperate seller do partial financing or buy down the rates...So if rates stay above 5% for the next 5 years I think 2 things happen: 1) More experienced/less timid investors have a huge advantage for a while, 2) eventually when everyone realizes this is the 'new normal' then things just go back to normal with slightly higher rates.But what do I know?