Help me choose a new bike!
Recently my 2009 Trek Allant was stolen and I'm now in need of a new bike. When I first got it, I was not a cyclist and I fully admit I just picked the first bike that looked nice without really knowing anything about it. It was just a brand I recognized at a low-ish price. However, about two years ago I got rid of my car and have been biking exclusively on that bike ever since.
Since my bike is now my primary mode of transportation, I'd like to make a more informed decision this time around. I still don't have a very high budget. Maybe $800, although I could possibly push it to $1000 if there was a really good reason to do so. Here's what my lifestyle looks like:
I bike to work and back five days a week, about two miles each way. I have a five-year-old son who is with me half time and I transport in a Burley Solo to daycare, karate, birthday parties, etc. He's getting old enough that I'm considering a trail-a-bike instead of a trailer. Once or twice a week I'll make a trip to get groceries or other small-item shopping trips using a set of panniers and a bike trunk. Since my bike is my everything, I occasionally have need to transport larger items using a flat-bed trailer. I have, in the past, transported items such as 2x4's, plants and other gardening supplies, a large window air conditioner, and a home theater system. In the summer months I make frequent trips to refill a propane tank. I live in an area where it rains almost constantly 10 months out of the year, so I need fenders (although I realize these can be added to just about any bike, but if the bike doesn't come with them, that's an extra cost consideration). In any given month, I can expect to ride predominantly on paved roads, with some bumpy sidewalks and gravel roads for a short distance.
Also, this is probably pretty important. I only have three bike shops in my town and they each only carry one brand of bike, so unless I can order the bike online, my options are basically limited to Trek, Giant, and Raleigh. If there are bikes from other brands that are a must see, let me know anyway! I might be able to find another way to get them.
Any and all input is greatly appreciated! I'd really like to actually take the time to learn why a particular bike is right for me, so the more information, the better! Thanks!