I have not lived in the property two years and feel that any profit I may make on a sale would get chewed up by closing costs and capital gains. 

Yes, it's true that you might be able to find a product you need at a greater discount when a brand like Wayfair or CB2 is having a sale, but I've found that they truly do offer superior discounts at scale, even considering the fee. 

If you were in my shoes, what real estate strategy would you recommend for scaling quickly (but smartly) so that I can replace a good portion of the W2 income from real estate investing?

If you’re paying off more than $1,500/mo I’d probably keep it barring any major upcoming capex. (3-5 years out so buyer wouldn’t automatically ask for it to be repaired at sale.)Good luck either way. 

I suppose you could share a portion of that with the cleaner if you are really desperate to keep her. 

He markets himself to no end and I see more stuff from him than anyone else, but he is one giant sales pitch. 

If you are in DFW area, do you recommend any meetups that aren't sales/marketing groups disguised as a RE meetup?

You'd think 60 years would have cleansed all that but it hasn't.You might target social service and local agencies since this property was in the past a half way house or similar and was only converted to market housing to make the sale to you.

The biggest challenge we faced is the property's proximity to a railroad, which has proven to be an impediment to the sale.

There is no seasoning requirement involved since the property isn't a short sale and it isn't someone buying REO from a bank with a seasoning requirement.