As long as you can later prove that this money did come out of your pocket, no issue.As far as your logistics question, let's flip it and consider it from the buyer's side.

While I'm excited about the potential, I'm also unfamiliar with the specific dynamics of the Orlando market.I'm particularly interested in finding a small multi-family property (duplex, triplex, or fourplex) that would be a good long-term hold.

There are a variety of formulas you can use, but to me, here's the bottom line from a legal perspective: as long as the utility cost sharing provision is not unconscionable, and the tenants agreed to it, they are responsible to pay their share of utility bills. 

@Wayne Brooks My lender said that as long as he's a licensed contractor, which he is, then he can do the work.

But, long term, you'll need to probably use a local credit union (or do forced appreciation with the bridge if its even possible)

I had issues with the tenant and we went through a long eviction process.

How long to get a tenant?

Critical Update: Waiting too long for the Fed to cut rates could significantly impact your approval chances.

My husband and I own a profitable condo we rent out short to mid-term, while living in a single-family home we plan to convert to a long-term rental.

Why wouldn't you be able to rent to a long term tenant?