It's a very old house but newly renovated so there has been some maintenance issues because of the cold and poor insulation.

You can't time the market. 

With a HELOC being around 9% I'd probably be paying more in interest than the money would make in the stock market.

You have to set them up, market, book and clean. 

Cleveland and Dayton can be great markets for high cash flow and low purchase prices, but you need to be careful when navigating the neighborhoods so you're not buying in a D/F class area where no property managers will manage and where you'll never see any positive cash flow.

There's a tenant that's month to month, rent is at least $800 below market rent, so I told the seller I need that unit to be vacant.

This is not to dissuade investors from building a team because I wouldn't be able to virtually wholesale in several markets without one.

Because they cannot afford the house or mortgage payment, and in many scenarios the rent payment is going to be the same or more than the mortgage payment.

Do you own your own house? 

Hopefully we will be managing a handful of other STRs in the same market in the future.