I'd like to start with rehabs and then transition into rentals, preferably multi-families; however, given my location and hours, I'd need to outsource essentially everything (though ultimately that would be the plan if I lived down the road, as well).

But considering outsourcing more of that as I grow..

I started doing it myself, but after about 30 minutes and not much progress, and realizing that The 4-Hour Workweek by Tim Ferriss was showing up often, I took a page out his book and outsourced this project.

That is a specialized skill set we prefer to outsource.

If it's a light turnover you can get it knocked out in a day depending if you are doing it yourself or you are outsourcing different trades (handyman, cleaners, landscapers, etc.) 

A lack of concern for the common good, and therefore laws and limitations on action & activity, inevitably leads to the insourcing of all profits and the outsourcing of all expenses.

Check out source before you follow someone's advice. 

I could outsource the management and go live in overseas or in rural America where a house is less than a VCR.

Consider taking a little less and out sourcing your PM.

However, we also need to see that we are not spending too much time (which is a resource just like money) on activities that could be outsourced to someone else provided that we could do something more valuable with that time.Having said that, since you like buying and selling things from Craigslist, I have a teacher friend who spends his summers (no work during summer) buying things from garage sales and reselling them on craigslist.