About 7 years ago my wife and I both bought bikes with good intentions at a top-o-the line bike shop. Mine was a fairly expensive Devinci Desperado
http://www.devinci.com/archive/2009/montagne/Desperado1.htm it came with tubeless tires, disk brakes, a lockout fork, Shimano XT group with some XTR components, etc. etc. Nice bike, but I never rode it.
SWMBO got a KHS - not sure what model, but it looks like this:
http://khsbicycles.com/12_vitamin_b_m_12.htm - hybrid tires, 18 speeds, side-pull brakes. Way cheaper than the Devinci, but totally different class of bike. She never rode it.
Then 3 years ago we got a bike trailer to haul the kids around. It was at a garage sale, and we had good intentionsof pulling out the bikes and bombing around with the whole fam-damily on weekends. Didn't happen.
Then I found this site.
I tried cycle-commuting and pulling the trailer with the Devinci, but the frame geometry and the gearing on the bike just won't work with the trailer. Add to that the trailer hitch slides back on the frame until it contacts the disk brake, and grinds. Really a bad scene. So my very expensive bike sits in the garage waiting for a mountain bike race to break out on my street. It is rarely ridden.
SWMBO's bike though - it pulls the trailer beautifully. Since the brakes are at the top of the wheel, there is no interference. The ride is way better suited to in-town cycling without the trailer. We replaced the seat with one that is more comfortable, and every now and then we tune up the cables, but apart from that, its been great.
Given the choice again, I would buy two hybrid/cyclecross bikes. Disk brakes are nice, but unneccessary. Suspension is nice to have but is an extra maintenance item. I don't really think you need it.
Agree with the other recommendations to look at Nashbar for accessories, but don't overlook the cycling section on dx.com either - its as good as cheap Chinese crap gets (we like the handle-bar mount cell phone holder for $5 in place of a cycle computer).
Personally I would avoid the bike shop route. I find the pressure to buy above your needs is huge, and you end up with more bike than you need. Also they will pressure you to get cool/competitive crap you don't need.
Check if your town is part of smart-commute or a similar agency to get free waterbottles/bike bells/gloves/jerseys/etc. for a free simple sign up. These agencies are common in Canada as an initiative to reduce vehicle trips in order to reduce congestion/pollution. The road to freebies is through their regular contests like this one (carpooling this month):
http://smartcommute.ca/carpool/