Sure occasionally they work out, but more often than not, probably not.

Some of the challenges:1) Pairing clients with properties that with an affordable plan yield the results the clients need2) Get the property into contract in this aggressive sellers' market with strong STR property buyer competition3) Deep due diligence to minimize property risk during inspection period + create best COE plan to yield the highest possible cash flow + start scheduling post-COE reno work4) After COE, get the hot potato moving- help in any way necessary to make sure my clients get this work done quickly and without complications so they can get their property on the rental market ASAP and start generating cash flow.5) Occasional STR audits as requested (always an option) by clients, to further boost their cash flow, and effectively their home value- based on income approach.

However, I like to hike, backpack, and do occasional remote trips where there is no cell phone service for up to 5 days. 

But occasionally, a repair would render the main bathroom unusable.

He stays in touch occasionally because his property shares a road and well with the properties I manage.

I don’t have a lot of maintenance calls because I do full rehabs on my buildings at initial turnoverBut occasionally there’s something that I deal with.

This is usually okay but occasionally when people are cutting it really close they run into issues and then either have to get mortgage insurance or put more money down.

Picking somewhere you'd like to go occasionally can soften that blow as well.

I have considered looking into other areas in my state that aren’t as competitive, but have also been intrigued by an out-of-state rental.My question: what experience/thoughts do others have about purchasing a property in a vacation area that will serve as an occasional vacation home for my family and myself and but will primarily serve as a rental - not sure if there is a term for it, but minimum one-week rentals and ideally snowbirds who will rent for a month-6 weeks or so during the high season.In my very preliminary research I have seen there may be some additional tax considerations but I’m wondering if this ever makes sense?

My expectation is that I will live in one unit, and keep the other unit for friends and family and occasional vacation renters.