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Every where you turn there are STRs going up on the market fully furnished because they couldn't pay the mortgage and bills with the rental income. 

The only “good news” is you’re paying for last year’s shortage and thsi year’s taxes, or this year’s shortage and next year’s escrow account. 

You want an investment that pays for itself, including mortgage, taxes, insurance, maintenance, and even some money set aside for a reserve to cover vacancies and capital expenditures.

With current interest rates, and they are at least 1% higher with potentially additional points for non owner occupied property, it is hard to find properties that will allow for positive cash flow after paying the mortgage, if you are looking for money for the down payment from a private lender, those are normally at higher than market and I am not sure it would be possible to pay it off.... please remember you need to take into account that you may not have a tenant for a certain amount of time, a tenant may stop paying rent, or you will have a big ticket item to fix, so I would wait if I were you and save to have enough for the down payment and closing costs and perhaps some money set aside for repairs. you also want to make sure that you have your own emergency fund outside of the money needed for the investment property because life happens ....

You can compromise without loosing good paying tenants if they pay on time. 

So why is the $2,500mnth person paying $250 and the other one paying $350 ??????

I would also share pros and cons of paying taxes on the windfall versus owner carry.

Keeping insurance and ownership in mind, what is the correct day to start the lease?

Do you want a company that will keep the long-range investment objectives in mind or one that focuses on today and today's profit alone?