This contractor will take me from gutted house to ready-for-drywall (reframing, new siding, finished basement, new siding, new roof, new plumbing, new electric, new HVAC), at which point I will take over and complete the internals with my team. 

Hello everyone, I wanted to get advice on transferring my rental property into an LLC in FL.

1) make the payment directly from my HELOC account2) transfer the money from HELOC to business checking account, and then make the payment from my business checking account.

But admittedly, I haven't been to small claims over a deposit dispute before (well technically I have but that was because a seller didn't transfer deposits upon the sale, which is a different matter).

moving it to an LLC will not do much for you in the way of asset protection OR taxes (double check that with a cpa, everyone's tax picture is different). most people lean towards the LLC thing for legal protection, but a single-member LLC is a thin veil that's easily pierced. you'd be paying LLC fees & paying another LLC tax return prep fee, for what i'd say is nothing. if you do want to transfer the deed to an LLC anyway, you'd do a 'quit claim deed' with a title company or real estate attorney. if the mortgage lender ever says something you'll just give them proof that it's a single-member LLC and the one member is you (the original borrower). 

I consulted with my CPA, who advised that the policy loan should be transferred to my LLC for private lending purposes.

I just got an escrow analysis from a new lender (transferred about a month ago) and there is an escrow shortage.

By the way, Tokyo BP Members - if you're ever headed to Seoul for a visit, be sure to shoot me a message and we can plan a get together.We have a BP member from the US coming to visit Korea next week and we'll be planning a dinner or coffee or something.Great to connect with other international investors!

Is it now an international city?

These same owners get mad when we do not start the project at risk and get mad at us instead of themselves.For internal teams, it would be that there is always so much stuff going on and frequently no person is able to be made accountable for the work that is or is not completed.