I wasn't sure if this was more appropriate to post in the commuting or recreational/family section, so I figured general was the way to go.
I haven't owned a bike in about 10 years (since I was a teenager), but am now thinking of picking one up for a few reasons. I live just outside Boston, MA, and I work as a freelance stagehand. This means that I need to be able to get to/from pretty much anywhere in and around the city, at just about any time of day or night. I have a car and live about a mile from a T station, so those are always options...but sometimes I don't want to deal with those for various reasons (such as traffic, parking, distance to a particular venue from the T, etc.), and it would also be nice to be able to get to/from that T station in less time than I could by walking or waiting for a bus.
It would also be nice to have around to just ride around for fun. I'm not looking to get into any serious cycling or anything like that. Figure on about 4-8 miles each way for work, with a lot of that being Boston city streets in varying states of disrepair.
I had mountain bikes for the majority of the time I was riding as a kid, so that's what I was looking at the most. I'm considering hybrids, as well. I spent most of my time on just the highest gear, though, because I liked the feeling of the resistance...so I guess I'm not terribly picky in terms of how many gears a bike has, as long as it's not a fixed-gear...I like coasting! I know I don't want a road bike, and I'd probably look out of place on most vintage-styled cruisers or a folder...not that it necessarily matters, but just imagine a long-haired metalhead riding something like that!
Here's one thing that might make things a little tough for me...due to the nature of my work, I prefer to wear BDU pants, with the legs tucked into a pair of combat boots (I like how they look, plus they're extremely practical for what I do), but I worry about the pants getting caught or rubbing against the chain. I'm guessing I should be looking into something with a chainguard? Or is there a high likelihood that I could find a suitable aftermarket one to fit any random bike? Changing clothes/shoes on-site isn't usually a reasonable option for me, so I'd have to ride wearing my work clothes.
I'm looking pretty much exclusively at used options, such as on Craigslist, with a budget of $150 or less. I've seen stuff like Trek 800s, a Giant Attraction, some Specialized Rockhoppers (my last bike was one of those, with 24" wheels), and various others.
I guess I'm mostly looking for particular suggestions of brands or models to look for or avoid...and if anyone local has anything that would suit my needs, I'm male, a little under 5'7" tall, and looking for a standover height no more than 25-26".