Risk vs reward for the bank.

That being said, the most rewarding part of this project is getting my family involved in the process.

I guess I'll just have to charm them into selling me their houses for my price instead of theirs...

Of course most investments are not guaranteed, so that's a more risky, but possibly more rewarding way to go.Of course tax consequences exist too.  

There's more chance for reward but much higher risk.

No risk No reward.

Often times you can be very well rewarded for this but that is the risk you take.

But even this is unlikely as you'll be buying at auction presumably without inspection.You can't expect someone else to take a big risk for a small reward.

This has been a rewarding and flexible career but I intend to transition that experience and insight into building a cashflow vehicle of my own. 

Its all about YOUR risk vs. reward tolerance, and personal goals.I personally would say unless you have already amassed some equity and cash reserves sell now and go  do the same thing again then you will have $70k then again and have  $105k and so on...keep doing what you know how to do until you have enough cash reserves to get into the long term buy and hold game and can afford to weather any storm that may come along.Good luck.