Before when interest rates were lower we could stretch LTV to 30% down instead of 35% and get close to what a buyer wanted for more yield.

If there are issues negotiate a resolution, you can ask the seller to put leave one in escrow to handle repairs but given how hot the market is that will be a stretch.  

I opted out of taking my commission on the deal to lower the sales price, after close of escrow I wish I had the additional commission to put back into the property immediately as I was stretched pretty thin for a few months.

Or is that just too much of a stretch, too likely to "get caught" if I don't bring it up and cause a lot of headache for everyone?

The house alone is not worth $390K by any stretch. 

I know this wasn't a home run by any stretch, but I think it has been a pretty solid start and am pleased that I was able to increase the appraisal by 45k in a year with 12k of work. 

Any other suggestions to stretch my cash in order to generate passive/rental income? 

If you think you could save the money in 6 months it doesn't seem like it would be much of a stretch to pay off a second on and accelerated basis.Another option would be to looking a HELOC or cash out on your primary.Lastly I think your plan to close quickly and then take out a second mortgage would work well.  

Most of my newer neighbors in this area have relocated from the Bay Area or So Cal citing slower pace of life, a desire for family-centric neighborhoods, and their housing dollars stretching much further.

Plus, most people take time off in the Thanksgiving through New Years stretch because that is what we are accustomed to culturally and we already have some free days off to combine.