I would like to know what all qualifies as completely clean here- Electrical wiring is normal and no unlicensed modifications - Structural inspection is also clean.Seller is ready to discount the price by ~20% from market plus the cost to repaint the whole house What are other questions to ask and things to consider in this scenario?

Did he low his job before you signed? 

Developing a team across state lines, cheaper contractors are not always best, they cost us time and money because they weren't the right people.

You could cost yourself over 7500 by selling it under market value. 

So if a property was offered at $500k, John might offer 2 parcels assessed value of $70k (cost him no more than $1k) and a seller financed note of $380k.  

The biggest drawback I am having is calculating cost for repairs & finding a reputable contractor for a fair price - I know nothing about renovations right now.  

I have no experience with flips or BRRRs and don't want to use all my equity for low cash flow right now either.

This can save you from costly mistakes.

At the cost, and given the benefits of most mortgage insurance offerings, is it worth it to pay (however much extra it is)?

If that property drops 5 you now have another $15k to come up with on top of the closing costs on that property.