In general, investing in an income-generating property first can potentially provide long-term financial benefits and greater returns.

First, you could ask him to sign a lease in which it states that he can be fined for unsafe acts in addition to other things you deem unacceptable.

It looks like a less labor intensive way to increase cash flow over the STR route but also includes structural changes to a single family home (additional setup costs) and dealing with low income tenants.  

The loan we were applying for is an FHA, which stipulates we must provide a signed lease for our half of the duplex (to be newly rented out) but for the other half which the parents "own" (in reality all three are equally owners of the entire property.) we would need to provide proof of rental income on our tax return, however her parents claimed that so we seem to be SOL.The mortgage is covered, we can rent it out no problem, but the underwriter is saying on paper it looks like she is responsible for the whole duplex and the rent for half of it is unreportable.

They are now offering a damage protection plan  and  cancellation insurance with an additional optional fee cost to the guest.

More on DSCR loans- DSCR loans won't use your income to underwrite the loan.

(or better yet, both)If it looks like your probable income will cover all expenses and debt service, you probably have a winner.

Additionally, I operate in neighborhoods with lower median incomes than 44119 (44306 and 44310) and routinely get significantly more in rent than section 8 will pay. 

You don't need to...markups in retail are pretty uniform throughout the supply chain, and for public companies like Walmart, you can look at their quarterly filings to determine exactly what their margins are.With contractors, you don't have this same level of transparency, so if you want to ensure that you're getting reasonable prices, you need to do some additional investigation...

In addition to managing a diverse portfolio of rental properties, we've successfully flipped several properties in recent years.