Loss History (see if you can get at least 5 years from the current owner) Ask them for "Loss Runs"5.

As such, I would be a little concerned about who will be your buyer if/when you outgrow your space or decide to move locations.Who is running the owner association?  

I called the number on the sharpie marker sign and a few days later I met up with the owners and walked the property.it's a well maintained (on the outside) duplex on a large double-lot with tons of parking.

I'm interested in hearing from Milwaukee-area property owners and PMs on what they currently wish they could outsource or are having trouble finding help with.

It really depends on your situation and you probably have low or small transfer taxes not sure of your exact location.In PA just transfer taxes alone depending on your valuations may deter some owners. 

Also, many times the old lease isn't signed over on paper to the new owner and then presented to the tenant.

If 2 business owners create a contract, are their signatures enough to make it a binding agreement or would getting the contract notarized be a wiser decision?

If you rent, consider up to 96.5% LTV owner occupied (OO) vs 80% LTV for conventional non-OO purchase.  

Would an owner occupant find this property desirable?

You may also need a different insurance policy since it would be a rental and not owner occupied.