I'm like John Wayne toilet paper. 

Most people don't have a single dollar in savings so when something big happens their finances go right down the toilet.

You want to be careful about how this is structured in most cases, although this sounds like a cool tenant you won't have an issue with....but you don't want a tenant to say hey the toilet has been running so I fixed it and will deduct X from rent. 

It's more specific than this breakdown, but basically rehabbing a bathroom (think attached/modified structure) would be a capital improvement deducted over time, but something like the cost of the toilet would be deductible this year as 'ordinary'  and therefore maintenance. 

I do believe that after making rent ready I’d be able to bring rent to current market value however this property being in Cleveland seems to have the same runny toilet issue no matter how many times we send maintenance.

In pan-Indian traditions, a guru is more than a teacher.

Fridges, ranges, HVAC, roof leaks, repaint and carpets at turnover, landscaping during vacancy, clogged toilet, etc: these things happen.  

Blocked condensate pan, dirty air filters, clogged pump, low freon, unit dying, vents not properly installed, air conditioning unit too small for square footage/airspace, exhaust blocked by plant material or stuff stored, animal inside the unit?

-Over $20k in water damages from a broken toilet that they proposed to fix when it was cheaper just to replace.

THEN start looking at raising some money.If this one does not pan out, again, start looking at how you can raise some money.