It was a nice property, demand was high How did you find this deal and how did you negotiate it?

I haven't really looked at AK as prices are pretty high in most areas that I thought would bring guests and that fact that it is pretty much a fly in area only.

If you have over-improved the unit for the market, it is highly unlikely that you will reap a higher rent price...the market just doesn't support it. 

We see it all the time analyzing deals in the market.Lots of investors are lured to areas like the Midwest, which might look tempting with its high returns, but don't overlook the ups and downs in occupancy.

(even more expensive due to volume and high overhead)

If you said that the property is in another state, then I'm assuming you may have to catch a flight, rent-a-car, food, etc....which will easily cost you more money than just hiring an inspector outright. 

@Tracy Scott it's highly dependent on the deal, the type of property and the location.In addition to the items others have mentioned, here are some of the biggest potential start-up expenses that I study closely before buying a property:Foundation/structure--this is one of my few "deal breakers", I typically will not purchase a property with significant foundation or structural issues.

I have seen local CPA's claim they can help offset high W2's with short term rentals here in LA.

I haven't been highly motivated, just wanting to get in the market when the right opportunity came along.  

You can use the costs of classes on a down payment and the time in classes can be used finding properties.All my high net worth RE investor clients don't use their degrees at all.