That’s also driving up prices at popular vacation resorts and other venues where people congregate.

My last resort would be to sell my house and get into a triplex with an FHA loan and then downsize to a duplex, and then SFH.

If the property is in a resort area the land can be worth more than the building.

I stayed at a deluxe resort in Mexico and they had heavy construction going on next door for the entire duration of my stay.

This is essentially what my wife and I do, but the opposite direction (aka, we have a short-term rental in VT ski country). 

Hello,Firstly, I'm a bit of a noob so please excuse if my question a bit all over the place.Backstory:I have a 1960's house in a small ski town where the real estate is booming.

Let’s take skiing for example:Some people will start their skiing pursuit by first doing conditioning in the off season, so they’re in great shape.

I'd focus on areas that already have ordinances that officially allow them, like Wheat Ridge, Arvada, Littleton/Highlands Ranch, Jefferson County, many mountain/ski towns, etc. or just go with medium-term instead of short term. 

Be sure to consider properties with year around draw or make sure the seasonal nature can cover the payments in the off seasons.Here in Boise, Idaho; we have such a shortage of properties, I know people that have resorted to renting nightly rentals for months because they couldn't find anything else to rent or buy.

You should be able to get the tenant to sign an agreement that in exchange for the two extra weeks they will leave by end of that final day.Waiting to see what a tenant is going to do can be really aggrevating, but the eviction process should be a last resort, and shouldn't be started if you've accepted rent.