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.  

And even then… i have seen home owners get less bc they lack stamina, negotiation skills, they lose money when negotiating for repairs… or they don’t know how to quantify a repair.

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).

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.

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.

@Jonah Hartsburg The FCRA says you must establish and implement written policies and procedures regarding the accuracy and integrity of information you furnish to a CRA.

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.

@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.