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. 

Her deposit covered most of her damages.

I believe we are late in the real estate cycle and there might be a drop in housing prices (which I am ok with), and in such a scenario I would like the rental income to be able to at least cover the mortgage payments and would be ok with paying for other costs out of pocket. 

If so, what gap(s) would the attorney fill that the realtor and property manager couldn't cover?

I believe we are late in the real estate cycle and there might be a drop in housing prices (which I am ok with), and in such a scenario I would like the rental income to be able to at least cover the mortgage payments and would be ok with paying for other costs out of pocket.

The parts were covered under warranty but the labor was not.

I know US LI covers more than 4 properties I tried calling up few companies but there was no luck.