lovelybike.blogspot.com has a great list of questions to ask before buying a transportation bicycle. Here are how I answered those questions a few years ago when I bought my commuter:
1. How far will you be riding on a regular basis and how hilly is the route?
First, I must say that the bicycle that I would buy would be multipurpose - it would serve as a commuter, a child hauler (trailer and bike seat, and, in the future, a trailer bike), and a light touring rig. Unexpectedly, it serves as a dirt road bike and has some long distance miles on it when I couldn't bring a second bike with me.
My commute is 6.5 miles each way. I live at the top of significant hill so a single speed wouldn't cut it. Sheldon Brown said I might use one, if I didn't mind walking my bike most days. I decided that I wouldn't want to do that and my wife agreed that would be dumb. It might have been possible to do an internal gear hub bike like the Linus bikes but I wasn't aware of them at the time I made this purchase.
2. How do you plan to dress on the bike?
I ride to work in either pants or shorts with cycling liners underneath so I look casual but I have reasonable protection. No need for a mixte but I am not averse to riding one (I owned a woman's 3 speed for several years in Madison, WI and it met my needs and was fast enough). I sometimes ride in full road cycling regalia but not when commuting.
3. What sorts of things will you need to carry with you?
Boys, up to 45 pounds (or whatever the limit of a CoPilot is) plus snacks and maybe a lock, depending where I am riding to. I need locks, computer, clothes, and lunch when commuting. I need a front rack in addition to a rear rack when carrying one of the boys. I also imagined that I would do some light touring at some time and still think that is possible (I have done some touring in the past, about 6000 miles worth on a number of different trips - it is something I dream about).
4. Where will the bike be stored, and will it require being carried up and down stairs?
No stairs. I ride it to my garage door or my basement door. I park it inside at work (in a bike locker) although I have parked it outside at work. I do put it on my roof rack. The bike weighed 27 pounds when I picked it up from Roy. It must be over 28 pounds with the front rack and the saddle bag which holds two tubes, tire irons, and a small multi tool.
5. Do you plan to ride the bike in the winter?
I am a fair weather rider. I might get caught out in the rain, and have, so I wanted fenders. No winter cycling for me at this time.
6. How much maintenance are you willing to perform?
Just starting to do my own maintenance - it is a money sink to have others do it for you. I once did all of my own maintenance on my touring bike, a 1984 Trek 520.
7. What is your skill level as a cyclist?
I'd like to think that I am quite skilled. I have rode over 35,000 miles since 1995 (so says my bike computers), and a lot of miles that went untracked before I bought my first bike computer, with no accidents. I tend to be very careful always and more so when commuting in the city. I have handled heavily laden bikes a lot in my life so I know what to expect.
8. What are your aesthetic preferences?
My aesthetics tend towards classic road frames from the 70's and 80's. I like the idea of flat (or flat-ish) bars but I have no experience with them so they may be a future addition to this bike or part of an addition to my fleet in the future. I like the fatter tubes you see on some custom Ti road bikes like IF, Firefly, and Seven.
9. What is your budget?
Depends on what I wanted and what I could convince my wife that I needed but it wasn't open ended. A custom frame was out of the question although I did think about it.
So, what did I get?
I had Roy Cervantes build a largely Shimano 105 build (racing triple) on a Surly Cross Check frame. The wheels are both 36 spokes although Roy advised doing 32 front/36 rear. The hubs are 105s mated with Mavic Open Pro rims - I would do Velocity A23 rims today. The year I had the bike built saw the Cross Check available in black and some ugly color (in my opinion) called beef gravy so I have a black frame. In fact the entire bike is black except for the drive train components, brakes, and brake levers. So it isn't exactly lovely but it has some nice lines, if you like touring/working bikes, and one day I will have the frame painted and it will be lovely. The bike has Planet Bike fenders, which are fine for now (I have some Velo Orange fenders on my road bike, which I could imagine on the Surly). I already had a Blackburn rear rack and Roy installed it for me. I now have a Tubus Tara rack, intended for panniers to carry snacks, clothes, and diapers for the bike rides with one of the boys in the bike seat. I just ordered a pair of Ortlieb classic front panniers. I have older Performance panniers that just don't work with the Tara rack.
I have put over 2000 miles on the bike in the last three years and it works well for me in all respects. I can get up the hill on the last leg of my commute, which is never easy but always very possible. I have no problems pulling a trailer with one of my boys or having one sit in the bike seat. Since I have toured some, I knew what to expect in terms of weight on the rack and have never gotten into trouble with one of the boys in the trailer or the bike seat. The Panaracer TServ Protec tires (700x32) are amazing. No flats and they do well enough on dirt and wear slowly. I rode single track in Harold Parker State Forest with my nephew and also rode the 2009 D2R2 on this bike with no real issues. I might have wanted a 32mm knobby tire (like the one that comes on the stock Cross Check build) for the D2R2 but did fine on the gravel sections with the Panaracers. It is great for the commute. I don' t race so I have time to slow down for the many potholes I come across. I can't avoid all of the potholes and the wheels and tires handle them well. I have slimmed down what I carry (I now leave shoes and clothes at work but that was more of a question of how to make the cycling/work transition work better and not to avoid carrying weight. The bike carries extra weight without me noticing it in term of ride characteristics. I have commuted no more than 100 times over the past three years (child care obligations limit riding days) but that seems a fair sample to judge how well the bike performs.
I considered a Surly Long Haul trucker but would be stuck with 26 inch wheels in my size. I much prefer the bigger wheels. I also looked at the Gunnar and Soma cross frames. I would have bought the Gunnar Grand Tour 2011+ version if it existed then. Having said that, the bike does well where I use it most. The big open question is how it handles loaded touring. I haven't tested it yet but know that it won't be a heavy load like some tours I have taken.
Well, not everyone will be switching bikes as frequently as lovelybike.blogspot.com, unless you have the flexible income to do so easily or the acumen to do it inexpensively (I have a friend who does this, bless him) so think as far into the future as you can. When I bought this bike, I did it for keeps so my thinking was long term and multi-use. I considered a custom frame but the cost and the idea of locking it up for 9 hours while I work wasn't really palatable. The Surly has a decent ride for low frame cost and has some flexibility. I'd love a touring bike for that tour one day but I can't see that coming until I take the boys, and my wife, touring across the country after retirement. But if I get the chance to ride to my friends' house in Ashfield, I have the bike in hand today. I would like to have a decent city bike like an 8 speed Linus but we have no room in the house for it, assuming that I suddenly had money for one. But I have a great city bike, if a little expansive for the purpose, already. And I have a great bike to haul the boys around on and they seem to like the ride.
There are a lot of great builders out there. I have seen Circle A Cycles, Sevens, Fireflies, and a number of other high end frames and they are all very, very nice. I am lucky enough to have a 2007 Independent Fabrication Club Racer (sort of, it is a modified version - mine can't carry a front rack) and it really makes sense to ride a custom built bike if you can afford it and you really enjoy riding.
Having owned 9 bikes before this one (over 45 years) and having a decent amount of experience on a bike, it was perhaps easier for me to select a bike for the purposes I wanted it to serve. But there are many, many options across a broad range of price points. If I had my way, I'd have a number of bikes of various kinds, all suited for the purpose. But that is in another life.