@Will F. This is a longish one so please bear with me.
If you're planning on buying and renting out, it would definitely make sense... and it would make even more sense if you put a team together who would run point for you IF you're uncomfortable (so to speak). If you're not from certain neighborhoods and you're not say, hispanic for example I can see how one can get intimidated. But by and large, in my experience, residents of these neighborhoods are way cool and go out of their way to make nice to obvious outsiders.
Case in point. Have you ever been to Lincoln heights which is the area around where the 5 freeway and the10 freeway split just east of downtown? Actually you will drive past Boyle Heights before hitting Lincoln Heights. These are primarily all hispanic neighborhoods. Incidentally, Boyle Heights used to be a jewish immigrant haven back in the 50s. The headstones in the cemeteries there tell immigrant assimilation stories by the last names alone.
Anyway nestled in Lincoln heights, is a very hipster friendly place that has been there FOR YEARS called The Brewery. Yes, it used to be a brewery years ago.
http://breweryartwalk.com/about
There is an art walk held there 2 times a year - spring and fall. I think I heard that there might be a 3rd added (not sure though).
Not too far away is an actual brewery called The San Antonio winery (btw)
http://www.yelp.com/biz/san-antonio-winery-los-ang...
Anyway, for some reason, this tiny oasis (The brewery) has been a hipster enclave that's been percolating for at least 15 years plus. I know because I had a place there for years while holding down a place on the westsside of Los Angeles. I just rented a place there because it was cheaper than renting a similar space on the westside. And then I found I was hanging out in a "hip" enclave.
That whole area is owned by a family called Carlson. Their grand dad bought a whopping tract of land back in the 20s and they have become bazillionaires from that land. They sold a piece to UPS and a small tract to land to the police dept.
That small tract was supposedly sold for 12 million about 6 - 8 years ago. It currently houses a bomb unit. Rotate the above link around and you see this: the PD bomb unit building (nondescript green building). Those gates open occasionally and some crazy armored cars roll out and head into the city.
If you keep driving east on this street you will eventually run into USC's Keck School of Medicine. Yeup, world class doctors and pharmacists training about 2 miles down the street!
'https://www.google.com/maps/@34.0659608,-118.21756...
Main street side of The brewery.
https://www.google.com/maps/@34.0659572,-118.21778…
Molton street side of The brewery
https://www.google.com/maps/@34.064797,-118.219507…
Art studios all up in that area
https://www.google.com/maps/@34.064714,-118.219549...
So my place on the westside was a hop, skip and jump away from my favorite places in Santa Monica and then I could get down and gritty so to speak at the Brewery.
The huge fiberglass horse you see sitting on the shipping containers was put there just before I left the brewery.
https://www.google.com/maps/@34.0659673,-118.21716...
And then in the smoke stack in the distance is visible landmark from the 5 freeway (which is directly on the left - (Main street exit).
https://www.google.com/maps/@34.0659731,-118.21676…
I haven't seen it before but behind this gate, there is supposed to be a fantastic Architectural digest type home with interiors that you'd see on say ABBOT KINNEY in Venice Beach. I'm told it belong to one of the Carlson kin but it might have since been sold. I'm told the house is made entirely of… get a load of this, shipping containers (=think MAERSK containers) !! Supposedly, it was featured in one of the modern home type magazines but I haven't bothered to find it on line. One day I shall.
https://www.google.com/maps/@34.0659549,-118.21893…
This (below) is a home owned by the Carlsons. Don;'t be fooled by the exterior I'm told it has a fantastic multi $$ interior.
https://www.google.com/maps/@34.0636606,-118.22007…
And the next door is huge UPS hub that UPS paid a kings ransom for (to the Carlsons).
https://www.google.com/maps/@34.0633289,-118.22023...
Finally, I just rented out a one bedroom to a UCLA med student 3 miles south of USC. Yes, this tenant was living in Santa Monica paying almost two and a half times as much to live in a 1 bedroom. I made sure the student knew that there would be a drive to campus in Westwood but this doctor to be wouldn't budge and moved in pronto!
All this meaning that if you screen properly and with a little luck sprinkled in, you will get quality tenants to fill your future place in these zip codes, some of which are leaning towards hipster gentrification-land. And we're not even factoring appreciation which seems to be unlike appreciation in the midwest (but that's another story I'm currently reading up on)!
All the best!!