(Whew talk about a hand cramp:) I am about to just outsource this in hopes of automating my business by going straight to the #1 source and contributor to people like you and me-yellowletters.com.

If your tenants work in factories that move to mexico, who's going to replace these folks.We are seeing 1970's style economy and they weren't outsourced then, Now the plants are moveing to mexico with no sign of recovery?

Longer-term Goal: I think there's value in self-managing at least the first property or two, to understand what it takes to be a good PM, but would eventually like to outsource management to a PM company, as my portfolio grows.

As @Bill McCafferty stated, I manage my outsourced professionals and control the deal.

Become a landlord and see how it feels, do you enjoy managing property on your own or do you want to outsource to PM.

For instance, you can send online invoices in QuickBooks desktop, and maybe outsource your bookkeeping to a professional who will enter it in monthly instead of annually before tax time. 

I am trying to 'outsource' by contacting agents and asking if theyd be willing to send me distressed properties if I provide them with a finders fee, but all of them kindly deny.

Most of the real estate investors I know, they outsource it to a bookkeeper that specializes in real estate.

Depending on whether you self-manage or outsource it to a PM will affect your expenses as will the age of the building. 

Because the time cost could hurt or the outsourcing cost could crush your profits.Best of luck.