If you don't own a garage, and you store your bike inside, you might want to consider the overall width. I live in an apartment building, with a bike room and roll-in access. Roll-in access doesn't help for a trailer that doesn't fit through the door, and many don't. This may also be a concern if you will be using the trailer in stroller configuration (usually an option) to do some shopping, as you should be able to roll into the stores where you shop. Most trailers' specifications say they are 32-33 inches wide, and there are many 29 or 30 inch door openings.
Yakimas fold into a vertical position where they can still roll, which would solve the roll-in bike room problem, but not the shopping problem. InStep's Ride-n-Run and Ride-n-Stride have specs that put them at 30.5 inches wide, which just might work for my door, but you should measure yours. The trailers from Tanjor also look narrow as the kids sit one behind another, but I don't have a width on them. Or you can go with a single passenger model -- Burley sells the Solo, 25 inches wide, and Trek sells the Rocket which I don't have a width on, but it is actually made by Chariot Carriers, who's specs put their latest single passenger models at 27 inches (Chariot Carriers actually puts a "Door Pass Through" in their specifications -- although in some cases it is narrower than the listed width of the trailer :-).
Make sure the folded size fits in the spaces where you need it to go, in the trunk, or the garage, closet, or shipping container. Keep in mind that the advertised "folded" size may also include removal of the wheels, which they don't include in the easy folding demonstration, so check for quick-release wheels if you need them.
Do not underestimate the importance of ease of folding. Adding an extra 15 minutes at each end of the ride can be frustrating, especially if you have to do it while watching your toddler.
If you will be hooking up to an older bike that can not be used with
quick-release wheels, make sure there is an option available.
InStep
uses an axle mount which attaches to a quick-release skewer, and I haven't
been able to find out if there is a fixed-nut option.
Burley has
both skewer, and fixed-nut attachments in addition to their frame hitch
option.
If it is a frame hitch, make sure it will fit. Many mountain bikes have a very tight angle where the chainstay meets the seatstay, so if the clamp has to go in this space it may be a problem. It looks like the Wike trailer hitches go into this space, but they also offer a quick-release skewer hitch. (In the case of my Scwhinn Twinn, neither of these will work.)
Also consider heel clearance, particularly for frame hitches. If it is bulky and sticks out, your heel may strike it with each stroke which is clearly unaccetable. The Rhode Gear/Bell Pro might have this problem. It looks like the Burley frame clamp stays fairly flush to the frame. If you have big feet, it is possible I guess that you might have a problem with axle hitches too.
Of course, for a rack hitch, you need a sturdy rack, and you then can't use the top of the rack while using the trailer.
Will you be using the trailer on more than one bike? Make sure there is a solution for each of your bikes. Some trailers offer axle hitch mounts that can stay on the bike, allowing you to quickly attach the trailer to any of the bikes that have the mount in place. Burley's combination of clamp, quick-release skewer hitches, and fixed-nut hitches should satisfy any set of oddball bikes.
You should get a hitch that permits the bike to fall over without toppling the trailer, as this is safer. This is probably a standard feature on all trailers by now, but ask anyway.
Two notable exceptions in the jogging department are the Chariot Carriers X-Country products and the Trek trailers (which are made by Chariot Carriers) -- these are well-rated as jogging strollers. If you look at them on the web, you'll see that they look like jogger strollers, with a large front wheel. Note however that this jogger stroller attachment would not be easy to transport while using it as a bike trailer. If you intend to ride somewhere and then walk around, you will probably want the more traditional (non-jogger) stroller attachment that is made by Chariot Carriers, and is also sold through Trek.
I think one thing worth considering here is what happens when your child falls asleep. When my son sleeps in our Rhode Gear/Bell Pro trailer the harness does a lousy job of holding my son upright (he ends up leaning very sideways).
Some trailers also offer the ability to recline the child's seat. Again, my trailer has this feature, however it is a major disassembly/reassembly process, and certainly not something you could perform with the child in the seat. I don't know if any trailers offer the ability to recline on-the-fly, but it would be a nice feature.
It's great if you can test the trailer with your child, although asking him or her to pretend to fall asleep may be a bit futile. Still, you'll probably get a good idea of how easy it is to deal with and how much your child likes it.
There are also a host of bike trailers out there that I don't mention here, and these tend to be smaller companies, or fairly generic trailers built by or for the name-brand bike companies. These trailers will tend to be perfectly adequate, but nothing special. They also tend to cost a bit less.
Look for large wheels. Larger wheels will be smoother on bumps than small ones. Spoked wheels are generally higher quality than the plastic ones.
Some trailers have a frame section that extends around the wheel. This makes the trailer wider, but can prevent the wheel from hooking on a post, or road debris. Some also have a frame section that extends to the wheel without covering it, for the same purpose. This is probably almost as good.
Make sure the cover gives you options for ventilation and protection. Flow-through ventilation is good for hot days. A screen in front in this case is mandatory to block bugs and road-debris. Plastic covers that can close the ventilation and protect against cooler weather and rain are also useful; even if you don't expect to ride in these conditions, sometimes things change.
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