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.

I'd imagine this is way lower maintenance than my other 2 duplex in the area that are 90 and 120 years old.

Usually a little lower for your primary residence.

Then again the only comp I could find for this went for less than this place.I'm on the fence with this place...If I could get a 50K price reduction from inspection, I'd be more likely to go for it, but as it is, it seems like lower end tenants with attitude, no cash flow, and a lot of risk.