We ended up having a well put in, which cost us nearly $10k and 6 months of downtime.

There will be downtime as well. 

Been checking into this during the Covid downtime.

I just feel like I am taking a step back if I end up going back to working for someone but the problem with wholesaling is there is a lot of down time and you can only do so many bandit signs etc..

In their downtime you could always have your employee searching Craigslist and any other methods, reaching out to them and trying to set up appointments with you to try and close the deal. 

I'm "Poor Mom"...although highly educated, working in a "great" career as an Information Security Manager for one of the top 5 defense contractors...I'm struggling to pay for family vacations or fly out to see my extended family once/twice a year just to get some down time without stressing.

Having to put 20% will keep a lot of investors solvent in down times.  

A floor being done in 3 days rather than 2 weeks is worth a lot rent down time.

There is a lot of down time and all of your basic needs are met if you can manage to make it to quarters, keep from getting obese and stay out of legal trouble. 2.

Conversely, at one point I paid $350 an hour for some sit-down time with a big time local investor going over his strategies.