Mistake #3 was not having knowledgeable people around to be able to ask questions.

However I am not as savvy as many of the people on here.

There are lots of helpful people in this forum and LOTS of posts to scour.

Happy to chat more or connect you with some great people in your area!

I don't think enough people consider this aspect.Selling Stock: Selling part of your portfolio could work, but the 15% capital gains tax might make this an expensive choice unless the stock has underperformed or you’re diversifying away from riskier investments.HELOC: Using a HELOC on an existing property is a flexible and relatively low-cost option.

I think others have given you great advice.For most people I say go to some meetup groups for a year. 

thats horrible, hopefully you can get some of the cash back. there are just horrible people in this world.

The area has certain advantages like shelter from regulation risk (pretty much as low as anywhere in the country if you buy in the approved STR tourist zones) and long term security (people aren't going to stop going to Orlando anytime soon). 

These are just deals I have invested in with other people. 

Now let's say one or both people making the purchase owned a condo previously where they roll over the proceeds/equity into the new purchase and put 40% down.