For example, west of 23rd St and south of the river, etc.2. 

A bit farther than these, but maybe more relevant is the South Shore REIA that meets on the cape just over the bridge and a meetup in Plymouth.I have not done a vacation rental so no insights on that.  

Doing 1000 letters in an area of south Kansas City going out over 3 weeks.

They come down to south Florida in the winter.

http://www.wcrt.org is another really good group.They have some subgroups that meet in the south suburbs as well.The one with Brie only meets in the city.

I'm looking at a potential job transfer that will be taking me from Milwaukee, WI to the South Bend, IN area (Elkhart to be exact).  

Moved to South Florida after college where I started a family and lived for 15 years. 

I'm not sure what areas you're looking at, but I know there are some pretty good deals in NE MPLS and South MPLS (by the lakes).  

We also invest in pure rentals, (south Carolina).Many of our friends have rented out their spare bedrooms allowing them to "pay" for their mortgage and often times utility living rent free. 

There is no way to predict everything in this business, but if you do get a note that goes south, PPR will do their best to make good.