Cleveland's strong rental market driven by a growing population makes it a great starting point ensuring a steady income stream.

Many of which are on a fixed income, and Dad is concerned about people moving in the winter when it's cold.

Are you referring to property tax classification, as in it moves you from residential to commercial, or are there income tax remifications?

What I would suggest alternatively is putting a clause in the lease that anyone above the age of 18 that's going to be living in the unit for more than 7 days has to be approved by the landlord and pass credit/background/income check etc. 

Need to understand your taxable income as well to know if it benefits holding them for depreciation.

Being 1099 and not having guaranteed income is challenging as is, I'm essentially dipping deep into my safety net to fund this project but the last couple of years have been great and I'm eager to get started.

I thought maybe she’d like the increased income and reduced liability as she approaches 90 years old but I see the tax issues might be too big an obstacle as she does seem pretty well off. 

I'll probably be here for another year or two, but I'll keep the property when I do find my next step, and aim for Mid Term rental, to get the higher income. 

I would prefer to do the upgrades so that it gives the property a permanent higher monthly income and hence higher evaluation if I choose to sell. 

With the realization that I could but and hold with some success in a military area, I decided that investing in real estate would be a good secondary source of income.