Bike Trailer for kids?

My son is 14 months old and I would love to take him on bike rides. I would like to buy the bike trailer. Can you please let me know what is important when it comes to a purchase of one. Did your toddlers like the bike trailer. What brand is good? I would like to spend around $150.00. Also, do I have to get a helmet for him?
 
We bought a bike trailer (stroller) on sale for $179.00 and I have an 18 month old daughter and she does like the bike trailer but our biggest issue is she still tends to fall asleep a lot when going for walks and rides. It just doesn't seem comfortable for her if she falls asleep. Especially with a helmet on (which is mandatory by our bike laws). None of the cheaper brands are that great - but they do the trick. If I had the money to blow I would have certainly gone with a Chariot.
 
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