Enthusiast versus Utility: One car to do it all, or two?

I'm somewhat of a driving enthusiast (although expenses of kids, supporting a family, have until now precluded getting anything too over the top)- currently driving a Civic Si hatch(was my commuter car until divorce...then my ONLY car) and always appreciate something a little fun to drive (and a manual transmission if possible). Life circumstances are evolving in my favor - and I'm looking ahead to my next car purchase (s), On occasion, I would like to tow a small boat (think sea kayak size, and I don't want to car top), haul bikes, or take 3-4 people for a long weekend in the next state. (My SO has a Prius, so that has helped for the trips with 3-4 for long weekends but no towing). So, I'm trying to decide between trying to find one car to "do it all" (thinking along the lines of a Acura RDX, BMW X3, Volvo V50 R Spec), OR...splitting the car budget and grabbing a late model used RAV4, CRV, etc., and parking it next to a used Honda S2000, E46 3-series BMW, Miata., or similar. I'd like to keep this whole adventure to about 30k for this round. I've been back and forth in my head - weighing the pros and cons, and thought I'd toss it out to the readers at Winding Road. In terms of towing, I'd like to stick to something that is actually rated to tow 1000 lbs min. As much as I like some of the VW offerings, I've been a multiple Honda owner since the early 80's, and kind of like the idea of something reliable and not ridiculously expensive to repair. (I know...I did list BMW above...not quite inexpensive) . I have to commute about 40 miles round trip to work each day. In favor of 1 car is the operating expense of two cars versus one (insurance, maintenance, an extra car clogging the driveway). The trade-off is perhaps a "jack of all trades...master of none" type single car. I might just have to take a leap and try it out. Have yet to drive many of these "one car to do it all" types, so that may be where the answer lies. Any insights and experiences would be appreciated. Sorry this is a bit long-winded - thanks for bearing with me if you're still following!
by MyTime on July 24, 2011 - 8:34 p.m.