I want to have clean documentation so the people renting know the rules and I have something to fall back on when I question is brought up. 

If this is something you regularly encounter with new tenants, I would recommend getting a checklist lined up for lease signing walkthrough so you can make sure all your points are covered before the keys are even handed over.   

I don’t qualify for an FHA or regular conventional loan due to the fact that I did a short sale in 2016 so I was asking him about doing a hard money loan.

My question really is would you let my current house look like **** being worth at least 350k and hopefully make the new house worth more because it looks so much better or just clean everything up and make both houses look great and raise property value that way?

A contractor that you know and trust with no history of such things is another story, where I would probably just let the contractor know I'd made a note of it and was giving them the benefit of the doubt based on their clean history - further explaining to them that I had to take that action/stance as a gesture to the tenant, and that I value their service.

Duplex tenants would be responsible for landscaping whereas the fourplex will require you to mow the lawn or clean the stairwell and common areas.I would probably take the duplex just because it would attract families with a little more money and probably have fewer complaints of noisy neighbors, parking, etc.

@Hakeem Valles I agree, we'd love to rent just to military members, but what is hanging us up is you can't turn a regular civilian away if they're qualified...

They will also work to clean up the property remove/tear down the existing shed structures that are unsafe.

Regular accountant is not enough.

I already stated in the P&S that the driveway and garage need to be cleared and cleaned by close.