Then I realized that the rent was about $700 below market rent and my expenses were getting out of control (taxes, insurance, mortgage, repairs) so for the past 8 years I was slowly increasing the rent every year.  

What repairs/improvements do you NEED to do, versus THINK? 

I am currently living in the property by myself and plan to rent the house after some essential repairs.

Hi @Tyler TomasAn appraiser can do a Subject To appraisal where they give you the AIV (As Is Value) and the ARV (After Repair Value).

I would use cleaning services but it's my understanding I could use more than one company over the course of the year to limit how many hours one company spends on it.I'm looking into a utilitarian STR more for business travelers, so this won't be one where everything is perfect, it's bound to accumulate wear and tear I think.The STR would be out of state, but I plan to travel there for probably two weeks a year where I would perform many repairs myself.

I’ve spent $51k so far in the last 65 days on property repairs and replacement.

I buy supplies, and keep up with pricing, do repairs, except for electrical, plumbing and A/C.

A distressed owner isn't about to upgrade and repair.

@Nicholas Halterman VA loans are great because you can do 0% down and continue to use your savings towards any updates or repairs you would like to do.

If one tenant moves out or unexpected repairs pop up, the other property can help cushion the impact.Of course, more properties mean more responsibilities...double the maintenance and potential headaches.