I don’t mind having skin in the game either, but I know using private money is key to scaling one day and would like to get some experience with it now, even if it doesn’t fund a majority of the deal. 

Keep in mind, if you're not making money, they aren't either, so they have "skin in the game".

That's why your having difficulty getting any valuation from a bank.

I’ve never had difficulty filing a claim with Airbnb as long as I showed the broken item and the cost to replace or fix it. 

I would guess that you have little or no experience running any kind of STR, and now want to get that experience on the back of someone else's investment, with little or no personal skin in the game, and that's not a good way to build an investment portfolio.

To expand a little on what is mentioned the underwriter's guideline, a DIL does not extinguish subsequent liens, so if the borrower has judgments against him/her/it that attach to the property, the DIL grantee takes title subject to them and may have difficulty getting them released later without payment. 

Hey Martti, Doing BRRRRs out of state definitely adds another level of difficulty, but it can be done very successfully. 

Quote from @Chris Seveney: @Francisco AvancenaThere are specific lenders who will do land dealsBut of course not as many as traditional real estate.The key will be skin in the game - typically for land because it is less liquid than a home the lender will want to have a lower ltv on the deal I fund land flippers currently in  CO FLA WA ID MT NV AZ OR TX SC GA VA  one thing about land though LTV is lower and RATES are NOT the same as typical HML rates are higher for raw land but its a specialty niche and a business that I grew up in..

A good one will also have skin in the game and will even be able to bring new acquisitions to your attention.

Hi @Shane Gorski,You're absolutely correct regarding the difficulties of STR's in Naples, there certainly are a few other local cities that are much more conducive to that strategy, Bonita Springs, Cape Coral, and Fort Myers Beach being a few of the major ones.