Challenges of remotely sourcing first rental purchase

[Chris Rosenbaum]

I'm currently living in Chicago, but only for sure for the next six months. I'm originally from the Philly suburbs, with lots of family in that area, particularly a few with contractor networks FWIW. My goal is to make my first rental purchase, either a 2-4plex or SFH, by late April. Took a bit of a parachute from a corporate role and not jumping back in full-time until May, so I have a pretty flexible schedule (at least 10-15 hours I can allocate per week if need be) in this time period, thus the motivation to get moving.

Being local in Chicago will allow me to see first hand a lot of properties, but it's most likely I won't be here much past May. I can't say yet where I'll be, but all things equal I'm likely back east for the long-term, and I already know that area much better. Do I sufficiently school up in the Chicago market and IL regulations and build a bit of a network here to start off, with the ease of seeing many properties first hand? Or do I start remotely building a bit more of a network and knowledge base in PA, trading the difficulties of sourcing for the greater likelihood of future footprint and leverage? I can be back in Philly a few times over the next few months when critical, just not frequently. 

My primary short-term goal is a profitable start, not extreme DIY value maximization in the perfect deal. I'm happy to leverage the beginnings of a solid local team (attorney, property manager, etc.) if the math works and it gets me momentum I can build on. 

Anyone try purchasing one of their first properties while not living in/near that area?