If rates fall, you can refinance the 2nd without touching the 1st lien.I wouldn't plan for long-term financing with the Heloc as the draw period will term out at some point.

Hi Todd, I have not heard of that one yet, but I like the term flip to freedom!

We have a single-family long-term rental in Port Charlotte that we'd like to keep the current mortgage rate, but we do have some equity we'd like to have access to. 

Therefore trying to get a bit creative with the financing.Positive cash flow will almost be impossible (as I'll have to probably take one bed away, and then build a bath and a kitchen) in what I've been finding, so Im trying to offset the mortgage as much as possible.Long term, ideally I get to keep it and the 2nd unit adds to the cash flow if I ever dont need it anymore. 

Just out of curiousity why would someone choose this model over a short term rental that is isolated by itself (privacy) or a hotel? 

Term life insurance.

Income is $600,000 per year and husband and wife both work full-time non real estate jobs.
Is it true that the tax benefits are greater, or realized more quickly, on purchases like furniture or televisions to itemize...

I'd prioritize finding long-term, reliable tenants who will treat your property with care over the quick turnover of short-term rentals.

Passive income is something talked about, but the majority of real estate investing is far from passive and what is called passive has payments for the passivity (management).Your why is strong, to provide generational wealth for your family and likely achieve time freedom long-term, that's awesome.

Own a few long term rentals.