Do you accept lower cap rates to be more 'certain' about long-term resale value? 

Some are a pleasure to work with and others I do not care what the potential is working with them I will pass.Anyone that adds tons of stress to my life or ultra difficult to deal with I don't need.

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). 

They just have a lower bar.

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.

Another strategy, would be to consider a cash-out refi on your primary, to do a larger down payment on one investment property, or split up the cash-out proceeds for lower down payments on more properties.