I had a harder time with the subcontractors like I mentioned, but that was more trial and error. 

Do some trials. 

If you're going part time I'd say limit it to a 3-6 month trial to see if you like the work before quitting your job - it sounds like you have some savings and investments, so rather than be mediocre and stretched thin, it would be better to do it fully or not at all. 

A 7 year old misdemeanor possession charge is not a big deal, assuming everything else checks out alright.Applicant must never have plead guilty, plead no contest, received probation, deferred adjudication, court-ordered community supervision, pre-trial diversion, or a have pending charge that has not yet been resolved for a felony of any type nor for a misdemeanor involving violence or sexual misconduct (whether or not resulting in a conviction).

Perhaps try out some different software, they should offer trials or at least a demo to see what works best for you. 

Its a trial and error thing until you get all of your own docs made up.  

Other than asking on BP or trial and error any advice for finding a a good contractor here in town? 

@Scott JaffaYes I use propstream as well and it comes with a free 7 day trial...pulls many lists, accurate comps, skip trace, RVM, email campaign and landing pages all in one place http://trial.propstreampro.com/lj

We’re trialing this, but invited the tenant to our ecobee.

More than anything this will keep you motivated and reduce the trial and error periods