If you are looking for multi-family it would make a difference in the approval amount since they will be able to add in average or actual rents toward yours or your brothers income 

I’m about to roll over a 401(k) to a SDIRA and I’m wanting to use funds to renovate a rental property that I already own that is in dire need of repair before I can rent it again.

I have dropped my rental price (from the original rent listing price recommended by my agent), but I still don't see much traction. 

I had quite a bit of money saved up from years of traveling and not really paying any rent as I was staying in hotels and accommodations paid for by my tours.

If you plan on renting as a second bedroom, you need egress and closet.  

Phoenix, AZ has been a great market for the past 10 years, but not so much in the past two years, as supply has really started to inhibit price and rent growth.

( both new builds and or rehab properties) I was not able to find any, rent to retirements has some in Ocklahawa which is kind of close to Ocala…but from what I read on the forum Ocklahawa is a lot more rural than Ocala, and not appreciated as much, is this true ?

Took this over from original owners at severe under market rents.

I am going to have my tenant pay rent online directly into my new checking account.

They're great when you live at the property, but can then destroy your anticipated cashflow if / when you decide to move out and rent all units.- When house hacking, be sure to establish a good relationship with your tenants, but avoid "being friends".