Here's why:This is a picture of a Schedule E.

Ensure you collect a proper security deposit (typically one month's rent in Florida) to cover potential damages.Your plan to increase rent next year makes sense given rising costs (taxes, insurance, and maintenance).

If they notice you have another house and your debt to income can't cover it.

If you sell your only overachiever to go with a more leveraged position, you could have 2-3 properties that may cover themselves or even provide a little profit, but when the rental markets shift (and they do), now you have 2-3 properties that all require you to supplement for their shortages. 

The down payment and I'll cover the rest with renting cash flow.  

Would it be reasonable or unreasonable to tell our tenants they need to cover the cost of the repair, several months after we had told them this guy would repair it for free?

The property listed for 200k, so we talked them down to 190k and they are covering 2k of down payment.

I still have a hard time understanding how this business model works for them, but perhaps that upfront fee covers for lack of deal flow (?) 

Lenders typically allow borrowing up to 80% of the home's value, which could more than cover your renovation costs.Fix-and-Flip Loan (Hard Money Loan) – If you’re planning to sell quickly, a hard money loan could be a good fit.

At $2450, it will cover those expenses.