I've quickly realized there's no quick way of assessing if a deal is good or not, you just have to run the numbers.

Continue to sell, I'm assuming you mean the assessed value, which is not a bona fide appraisal, and if you were trying to sell on market for a year and a half for less than what the new assessment came in at it obviously isn't worth that much. 

License can wait and you will assess yourself if you need it once you are sure with your goals!

This might be a good topic to re-assess in 3-6 months

@Russell Holmes is spot on with his assessment.

When my local government feels generous enough to forgive my property taxes , water bill and front footage assessment , I may think about it . 

Pay back LOC to $0 set back property reserves and have a fair lump sum to add to LOC to get the next bigger and better deal, scaling up each time.Does anyone have experience assessing some of these values?

Personally, if I had a contractor who understood value adds and simply was giving me an honest assessment of his opinion every once and awhile (without being pushy), I think I would be very happy with that...especially since he's providing quotes at the same time.

But Before you accept an oil tank "as is" I'd do a careful assessment. 

While searching through some properties in my focused region, I came across a foreclosed property that was listed for ~$148,000 at the end of last year by Auction.com, but was later bought in Jan 2020 by FV-1 Inc for ~$13,000 (according to county assessments).