However, even getting this done takes a lot of maneuvering and there's a risk the seller will send a third party to secure the property when they realize its vacant and they still wont allow you access.

It really depends on your long term goals, your own personal risk tolerance, personal management tolerance etc. 

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.

Why risk it for a fairly minor cost savings?

And all my family members are very discouraging about the risks involved in realu estate.

I am willing to take some risk, but my income pays the bills.....including the mortgage.

Personally I would not carry the higher risks of renting a SFH, especially now, and I would be selling to invest in multi units...each to their own.

If it is not a profit center for you that has no risks it is not something you want to be involved with.No way you want to be dragged in any child porn charges etc.

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?

One reason for this is we have 2 young kids (3yrs & the other is 1 month) another is because well it’s a risk...