However what happens when the tenant vacates and now the unit has to be turned over/takes a few months to find a new tenant and during that same period of time the sewer line goes and you get hit with that $15,000 cap ex expense in addition to the vacancy and turn over costs.

Forget the course and put that money on a quality vacation short-term rental.  

As our team has grown, it's become easier to cover responsibilities if someone quits, goes on vacation, or if we terminate employment, compared to when we had one or two homes. 

Sure it does. but depending on who the celebrity is/was.....That's why so many little hotels, boarding houses, vacation rentals, etc..... feature this in their advertising.And in some cases, you will not get more money, but you will get more guests.A little while ago, I went to Tombstone AZ and stayed in 'The first boarding house in Tombstone'....really cool place but kinda small and, well....old feeling.

Our buy box specifically focuses on vacation destination accommodations - including boutique motel/hotel, campgrounds, treehouses, cabins, etc.   

My goal is to live in the home during the winters, maybe 3-4 additional weeks for vacation, then rent it out to help cover the mortgage the rest of the year.  

., known for its upscale appeal and strong demand for vacation homes.Properties in the Hamptons attract affluent buyers and renters, offering a high potential for appreciation and steady rental income.he property may have been undervalued due to its condition, presenting an opportunity to add value through targeted renovations.

All a mid-term rental is someone staying not permanently but longer than on vacation.

Rodrigues' recommendation may change this), but my next question would be, are there any cities/markets where 1 of the following are true: 1) You have family/friends that live there, 2) You travel there frequently (either for vacation, work, etc.), or 3) Somewhere else you've lived before AND know the area well?

An example might be a commercial tenant with 50% of the space in a building sends an after-letter notice that it now plans to vacate at the end of its lease term in 6 months.