On a similar home,price, neighborhood etc.., Norada will say cash flow will be ~$400 and Roof stock will say ~$100.

.) - you should be OK but it would behoove you greatly to get some sort of documentation like a BPO (Broker Price Opinion) of the value now for use later in the refi!

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?

Looks like the only option to do a break even or cashflow with current prices in the area. 

Through Host GPO you can get high quality items for an affordable price. 

Prices have jumped up pretty significantly the last few years; I had an addition done in 2021 just when lumber was starting to go berserk and I spent $100/sf *BUT* I use a lot of these contractors in my rental business and it wasn't a turnkey job - I did the electric, insulation, HVAC extensions, painting and trimwork.

Just for more details:- At the current listing price, my monthly payment on the property will be $6000.

I have had a couple of opportunities to market similar properties time on the market, desirability etc and having a sharp property with decent ceiling fans helps.I think it depends some on the property and the target audience as I have investors with lower priced multi-units with no fans on purpose that work out very well. 

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

Down side the houses in this price range are older and possibly not in best neighborhoods, more repairs possibly harder to find good renters.2.