I really do appreciate your experience with similar situations and seems as though we're not missing anything here and on the right track.  

and the permitting process might be cumbersome. but similar to the roof, get some quotes and do the math if you want.

On the right are four similar properties.

As luxury vacation short-term rental hosts, has anyone faced a similar situation or have suggestions on how to proceed?  

As time passes I may have to drop it but there are similar (less cute) homes for less.  

.- Any potential pitfalls to watch out for during this process.If anyone has navigated a similar setup or has referrals to professionals who can help, I would be extremely grateful for your input!

similar question - I don't think the deal finder tool is accurate - how are they sourcing the data? 

My goal is similar.

After reading and talking to my lender which didn't offer it (similar to what @Drew Sygit said) I went the conventional route and used cash for the remodel. 203k loans have hurdles, payment draws, specific contractors (grosssss), and other requirements that slow you down or cost money.Investors have found success with (203) loans it but consider your overall goal, budget, and timeline. 

In other words, it's much cheaper to rent in my market than it is to buy.If your numbers are similar, you could rent out your primary, live in a rental for cheaper than a mortgage (especially if you downsize), and save up for your next primary.