You’ll want to make sure the rental income comfortably covers the new mortgage, taxes, insurance, and any maintenance costs.

I'm an authorized reseller for Generali (for our guests that book off-platform) and it's something like $59 for the guest, and you can buy it on their behalf, but I'm not sure that it covers chargebacks.

Ask for a "Pre-Underwrite" this is where the bank underwrites the file and give you a "Loan Commitment" instead of a generic "Pre-approval" letter.

We don’t know any PMCs to recommend in the area mentioned, but since selecting the wrong PMC is usually more harmful than selecting a bad tenant, you might want to read our series about “How to Screen a PMC Better than a Tenant”:https://www.biggerpockets.com/member-blogs/3094/91877-how-to-screen-a-pmc-better-than-a-tenant-part-1-services-and-processesWe recommend you get management contracts from several PMCs and compare the services they cover and, more importantly, what they each DO NOT cover.

The answer is yes, 2nd lien DSCR loans exist and more than one lender can do them, but you would probably have to up your credit score to be able to get up to a total of 75% ltv between 1st and second lienOtherwise, you would have to get lucky on a favorable appraisal.

Used an existing frame down in Belize to build our house down there.  

He can't loan you any part of the 3.5% down and you can get seller contributions to cover closing costs, etc.Just food for thought...

Patience can be your best friend and if you attempt to over leverage a property it can come back to hurt you.Some will recommend buying subject 2 where you could take over an existing mortgage that could be at a substantially lower rate - but if the lender finds out and calls the loan that could also be very bad.

Pre-covid it was around 1M visitors for a 3 day weekend festival.

That is assuming your DTI can cover the increased mortgage payment.If you have use for that extra $100k that you would get back right now then don’t wait.