That's tough in today's market but not impossible.2.

Finding a good contractor is damn near impossible.

Of course, it can be almost impossible to validate any rents the seller claims theycollected in cash.

However, that isn't impossible to do if you go that route. 

Kauai is an expensive market with high overhead but I have 15+ years of solid returns so ignore those who say its an impossible market. 

Everything else takes twice as long as it should take anywhere else. 20 years ago I had a developer in my office that had just relocated up here from Florida and was complaining about how long everything takes, how slow subs were, and how impossible it was to keep anyone on payroll.

Though impossible to measure, and a fraught investment metric there is a certain emotional capital gained by creating something beautiful that you love and can enjoy.

Talking to zoning officers, I find that in some municipalities they are grandfathered in, but in others this exemption ends when the lot changes hands.What I am seeing is a picture of a huge amount of semi-rural land that is frozen in time—impossible to use and therefore impossible to sell.

The company I mentioned before (iMortgage) does $35K max VA renovation loans that can be used for any kind of renovation, similar to the FHA 203K Streamlined loan.This means the only base I haven't covered is a renovation loan that allows for more than $35K (not new construction), similar to the Full FHA 203K loan and the conventional Fannie Mae Homestyle renovation loan.It took looking around a lot to find just the two I've found so far, so it's hard, but not impossible to find lenders.  

These rules made it very challenging–-and frequently impossible–-for investors and others to operate non-owner occupied STR properties legally in Austin.