Hi Marcus,There are many ways to skin a cat per se lolPersonally, I'd rather have volume and 10 "in da hood" where the numbers don't lie and where I know what I'm doing.Then buying using a tonne of leverage and hoping the market will appreciate."

I don't know your skin thickness but know I do it with love and care for your improvement, there is no insult meant by any of it but fact is we all gotta suck, learn and try again before we get great, right. 

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

I doubt if anyone is saying it's impossible for it to work but I feel it's difficult. I

That way you’ve got some skin in the game, and the tenants will be less likely to protest that the other tenants are using more electricity or gas.

If so how difficult is that?

There are multiple ways to skin a cat.

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.

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..

You likely will max out before 10 though as the average person with average income will have difficulty qualifying after a few loans because of things like the DTI (debt to income ratios).