Tried in vain to figure out how to add a bedroom on main level  - no go.  9 foot ceilings in basement but big money finishing didn't make sense for flipping. 

You add in subjectivity of someone's level of experience or education, things get messy.

When the property went off the market a month or two later I found out who owned it, eventually got in contact with the owner and bought it without us using agents (no 6% = a great bargaining chip for a lower sale price). 

Sounds like you are ready to kick start your portfolio to the next level!  

They just have a lower bar.

Honestly, I think your best bet would be to really focus on your credit for now until you can get it to a level that is sufficient to do a HELOC or a home purchase.

The house that got me to reach out to the owner is in a fine neighborhood, split level ranch in a mid to upper class area. 

On the ground level as I am-it’s obvious.

IMO the lower quotes aren’t always for inferior work and in fact are sometimes very good, small owner operator types like that if they work quickly and efficiently can get things done for cheaper, and having a general handyman that is good is invaluable. 

I am thinking about either asking the seller to repair the big issues first, lowering the purchase price, ask for a credit at closing, or a combination of those.