The Cash-out Refinance loan will cover the $250,000 Purchase price and $50,000 Rehab. 

Covering all bills, cleaning, maintenance, etc.

I want to make sure im covering all options and doing what I can to be an asset to people.

I do not think I have the funds to cover an entire conversion at around 4-9k.

I would only want to consider taking a loan of that size however if I was CERTAIN any investment would generate enough income to cover the carrying costs.

If they are having you make PITI payments and the rent does not cover this and fees are the owners sending you checks?

Sure - as long as the benefit of the Series is sufficient to cover those costs. 

When it comes to utilities if you can not have them in the tenants name paying directly you are better off just raising the rent, plus some, to cover any anticipated costs and look into properly dividing the utilities with their own meters.

I would ask for actual numbers (gross revenue/net revenue) and see if it makes financial sense for you.You'll need insurance that covers vacation rentals which most carry now - just ask your current provider if they do or don't.Other costs:Registering the rental for the short-term license, Florida sales tax, and all county taxes.Will you be self-managing or hiring a manager?

If you can take that 10k and somehow turn into a place to live with roomates that cover your expenses and put money in your pocket I would go for it.