May be worthwhile to self manage the first building and outsource thereafter... experience goes a long way. 

I can't have an empire if I do all the dirty work myself--I have to outsource in order to build (and to be hands-off, which I also want to be).

It's the leaving party's job to secure their exit without damaging the company.As you said, make sure you document roles and responsibilities of everyone, if property management is outsourced, insourced, who makes decisions, blah, blah, blah.

Any tips are very helpful, about to start outsourcing labor instead of doing it myself.  

fulfillment/outsourcing ain't much more than what you're paying manually doing the work for each postcard.Couple of questions that are important to the whole direct mail process:1) Is it scalable (manual letters aren't)2) Are you using your time in the most efficient manner (handwriting is ok for starting, but you need to hit 1000s of targets to get the responses to grow your business)3) Is your message correct for that market?

Per your advice, I would need to also account for Maintenance and Property Management costs...still trying to decide if I'd manage myself or outsource. 

Purchase properties on your own and outsource ongoing management to a 3rd party property management company (in this scenario, you would need to find the deals)

Maintaining your own staff means you have to carry workmens comp insurance,  have payroll taxes, and payroll accounting to do (or outsource). 

I want to compile these for my own portfolio, so when I wish to outsource for investor funding, they can see my experience. 

I want to continuing managing my properties long term, although I've had to outsource more and more pieces as I grow.