I wouldn't think of it as not being self sufficient just a way to help you scale faster.

Generally speaking, yes.There is an argument to be made that you develop wealth faster in more expensive markets.

Basically, rental prices will push up faster than mortgage prices tightening it and making it more "affordable".  

Hopefully this allows you to your market faster or another faster and move forward

I know 30k is a lot of money but depending on your goals and how fast and big you want to grow, a good mentor who has been there can catapult you there faster and help you save money from mistakes you might of made on the way.  

There is less to risk, they can be completed faster, and the rehab is easier.

Some of my clients think if they have more than X number of guests in the house, it will wear faster, and they want to one day occupy the house full time, etc etc. 

I may consider a 6 month minimum through airbnb but anything less like an STR is too much for me, especially given how updated the place is, the turnover will get it deteriorate faster 

If you are trying to build a portfolio, your growth will accelerate much faster if you can build and grow equity through highly appreciating markets and value add investing.

He works on his own time and schedule, with little supervision except time and time again I happen to be there to make sure he doesn't fall or get hurt, as well as just to help the project get done faster and move onto the next.Sadly though, it seems since business has been so slow with his father (he metioned his father hasn't paid him for the little jobs they do (for other clients, not me) together these days).