I think there are certain elements of meetup groups that aren't desired such as the unsolicited sales pitches from tradesmen and/or the group having a clique feel. 

If something that was done "manually" is packaged under some new technologies (web 2.0), would you consider that emerging/latest?

Keep 'em rolling!

Since most folks search over the web these days,,,,long distance advertising is not an issue. 

He helped us migrate a handful of pages from hostgator to microsoft and helped out with a whole bunch of email issues and web site hacks ( before we found him!)

Is it worth it to hire a web designer when there are YouTube videos that, for the most part, teach it?

@Vince Lucas  one thing I can tell you also from experience first hand is contractors are much better and reliable in Cleveland than FLA.. they tend to be very transient in FLA and not so much.our guys know em out in 10 days or so in Cleveland lucky to rehab in 2 months in FLA.. with the contractor base there..

I would (and do) self-manage properties in my backyard.  3 dozen of 'em. 

Statistics and web reviews can only provide so much information.

Go get 'em man!