With VRBO, strangely, it keeps recommending significant increases which isn't wrong.

Hey Rafael, as someone who's been investing in Florida for 20 years, especially in Tampa, I'd say you can’t go wrong with focusing on this market—it’s got strong appreciation, great rental demand, and tax-friendly opportunities.

I understand that the tenants will paying me money that i will put towards paying off the house but it just seems like so much could go wrong.

If I'm wrong in my thought process like others I'm here to hear the best advice for all of us :) 

What precisely went wrong?

If you are nearby, if you have ever been a pizza delivery person, maybe deliver a pizza to the wrong house that may or may not be the one being foreclosed on so atleast you can see inside a small portion. we used to just go knock on the door some folks would actually let you look around.

A local couple who’se combined income is 300K and who sponsored the family’s immigration to US is willing to be co-signers for the family of 5.I am thinking that Party2 will put more miles on the house and may be harder to deal with in case of any complaints or eviction, though I am not an experienced landlord so I am not sure what are the factors to evaluate or what all can go wrong?

If you are trying to come up with a way to finagle the occupancy requirements while using an amazing loan (that you earned based on your service) like a VA, I would say you are starting off on the wrong foot.

I own real estate investments and I own other asset classes like stock, crypto, etc. and there are pros and cons to all of them.I will say there is nothing wrong with selling your property and utilizing the cash elsewhere.

It sounds like the tenant has solid evidence their check or auto payment was received by the wrong party.