Im actually considering buying some properties there myself at some point since I already have a good network there (i.e. an agent, a property manager, a hard money lender, etc).

I'd start there and then develop  relationships with lenders that specialize in that space.

While it depends on your financial position, I would recommend working with a conventional or DSCR lender and/or exploring the option of utilizing a HELOC. 

Especially if the lender wants a balloon at some point?  

This varies by the lender.

It's an overlay...the guidelines are minimum standards for a conventional loan, it doesn't mean that a lender has to give you those loan terms.

Any lender or investor has experience on this?

One caveat: doing this created a situation where it was difficult to get loans because one of our LLCs is a "checkbook IRA"- seems the nonrecourse lenders mostly don't like having a non-IRA partner involved.

Assign a power of attorney to sign in the US (the POA will be signed with a remote notary - and also that some lenders did not allow)2. 

I reside in Massachusetts and my boyfriend and I want to purchase a vacation home in a specific resort in Davenport FL. Our primary goal is to have a long term investment that pays for itself (or at least offsets the ...