However, on the renting side, we have seen an increase in inventory of days on market too. 

How much will the increased cashflow supplement your anticipated SSI?

Partnering with investors to share profits is another avenue to increase capital.

You can also expect increasing HOA fees, and there may be some problems renting a property inside a difficult.You don't have any experience, prices are at an all-time high, and rates are also high. 

They have increased in value, and our rents have increased by more than 45% overall.

Canton is not quite as bad, although they have increased annual fees and initial inspection requirements in the past few years that Akron never put in place. 

The fix-up and increased value will not matter to the IRS as long as you sell within a reasonable time frame of the house passing into the estate.

I would be cautious buying in the saturated areas because there are so many similarly sized properties that price is becoming increasingly the deciding factor. 

Just make sure you are saving towards those slow months during the peak months, buy a deal at the right price (don't overpay just because its a turnkey STR or you think it will make more money than projected), and look into ways to increase bookings during those slow months with some marketing and operation tweaks. 

I have clients who are increasing their cash flow by between $19k and $55k and their cost basis is between $145k and $200k.