But there is also the factor of what do I want to with the rest of my life where the only pathway may be schooling and if you truly accomplish that by going to school, the money might not be so important.

@Verletta Saxon what are you trying to accomplish? 

@Steven Cowles  If you have done 12 successful Flips, I'm surprised you are so hesitant at your ability to achieve a successful buy and hold to be honest.  12 flips is a great accomplishment and you should take that energy and confidence into your buy and hold investment.  

And I have been exploring the right software that can help me accomplish rent collections digitally.

Then come up with a plan of exactly you want to do and accomplish. 

My question is (and forgive me if this is an ignorant one), how do I accomplish this during the purchase process?

Hopefully good jobs will give people the feeling of self-worth and accomplishment so they don't feel the need to do drugs! 

What an accomplishment!

It really all boils down to what your strategy is and what exactly you are trying to accomplish.

We built a pretty strong team that understands what us BP members are trying to accomplish. congrats on your first househack!