I declined the vacation/deal trip. 

High-speed internet, a desk, good coffee etc will be different than a family staying for a vacation. 

And most of the damages a guest will do can be covered by these str booking sites insurance.Your budget will prevent you from buying homes in some of these big cities or vacatation areas with tons of str's. 

Also what type of lifestyle are you trying to maintain-a simple one or one where you go on exotic vacations every month?

I'm seeing 25-30% for STR management in Colorado (more if your vacation rental is near ski areas like Breckenridge or Vail). 

People who are able to work their business or job remotely will choose a vacation style locale to live like Florida where we have great weather, no state taxes, and a very low tax rate compared to other states.

The good thing about househacking a legal multifamily unit is that lender allows you to use the vacated units of 75% market rent as an income to offset the potential current mortgage.

At that point, if your tenant is not willing to renew,  you simply advise the tenant that you will not be renewing their lease, and provide them a move-out date by which they must vacate the property.  

There would never be an issue there to stop STRs as it is a vacation resort.So, if you are looking at a condo, make sure that you do your due diligence.

Vacation rentals are tough!