-My recommendation is always that, if you're thinking about investing in Toledo you should spend a couple grand on a trip to the area to see the market firsthand.

I'm in a fairly small city about 45 minutes outside of Savannah (Hinesville by Fort Stewart), so the cleaning companies in Savannah haven't wanted to make the trip to clean my rental.

I live in VA and love to go down to Boone and Asheville on a long weekend trip and always stay in VRBO or Airbnb.

Because there wasn't a whole lot going on in the area if you weren't hiking or day tripping into the woods.

., I would list it on both AirBNB and VRBO/HomeAway and probably Trip Advisor.

my questions are these:sf bay cities like san jose often have better deals (lower GRM, good economy, good transit for the next gas crisis) than marin county. it's a 2.5 hour round trip drive there, tho' and i DON'T know local trademen like i do here. aside from having to find a property manager (which i gather may be tough) what are the upsides and downsides?

That is your liability.When you rent it: your tenant trips walking up the stairs and breaks an arm.  

I am looking at the Raleigh area because I am familiar with the area, I can travel to and from when needed, and I could even deduct my travel from taxes as visiting my family would include a trip to check out my property (and thus be a business expense).

Eve in those neighborhoods though, it is street by street, so I recommend making some connection in Memphis, take a trip out there, and let everyone know what you're looking for.

Good luck on your trip.