We could work backwards from the condo's upper tier pricing (that you would likely get into contract at) and backwards calculate how much income you're going to need to qualify given the probability of how the rest of your rental income and liabilities will be caluclated.We do these calculations (plan A, B, C, etc) on a daily basis.

The current GM does a lot of the leg work, I think I have opportunity to capture the marketing and booking dollars spent by doing that work on my own. 

After my research I no longer wanted a new fancy ready to go home, I was looking for a fixer upper.

Make something unique, then get ready to do a lot of additional leg work and searching!

Upper Unit got broken in and they stole the new hotwater heater, new appliances, and air conditioner..... damage flooded upstairs and downstairs units.4.

Heights I don't think you'll find under 350k unless its a fixer upper

I may buy in the upper jungle/cloud forest and then keep renting where I am currently since prices are dirt cheap.

It is almost as hard to buy a fixer upper at a price that will cash flow after repairs. 

Has anyone had experience with this issue and know a way to get a good insurance policy that doesn't cost an arm and a leg? 

Once you get into the 5+ unit properties, the lending market evaporates, there are very few lenders in this market and the rates are 1-1.5 higher than in the 1-4 unit market, if you are thinking bigger, the 10+ unit financing is best case 65% LTV, where the 1-4 unit market is 80% LTV for  Stabilized rent ready properties, and if you are buying a fixer upper you can usually get 90% of purchase and 100% of rehab.