Well, I bought my Raliegh at Get a Grip Cycle on Irving in the City (I’m from the burbs, but know the owner from a previous purchase) and they are REALLY helpful there (even have a professional fitter for bikes. You’ll probably feel more comfortable with a lesiure bike (not mountain, not street, but inbetween) with a step over option (the bar isn’t high where you have to almost angle the bike to get on, you litterally can hold the bike straight and step over. Also, I agree you should go for the more expensive brand that you can find at a professional bike store (not at Target) because of the quality (not to mention, the smoother ride). Also, I have the Topeka bike seat for my dd (holds up to 40 pounds) which the bike shop sold to me and installed (I wasn’t comfortable with installing that myself). My dd loves going on bike rides with me but I worry about what I’ll do next year when she’ll probably be over the weight limit. YOu can also buy a trailer to attach to the back of your bike and your little guy can sit in it, but it is close to the ground (which is the reason I didn’t buy one - we ride on the Prairie Path and Great Western Trail and b/c of her asthma I didn’t want the dust to constantly be flying in her face plus I want to talk to her and be able to point things out to her along the way). Either option is good for your son, especially because he sees how important exercise is. Also, depending on where you live, depends on how intense a ride you’ll have. Since you’re starting out, it may be intense on the easiest levels/speeds, but as you get better, you can challenge yourself with tougher speeds and longer distances (I once rode from Villa Park to Rt. 59 and let me tell you OUCH!!!). Also, make sure you bring food, id, and a cell phone/money for a phone, just incase something happens. Also, I bring a fanny pack first aid kit with me on my rides, but I tend to be a worry wart. And NEVER forget water. Maybe start by riding to the local playgrounds with your son, and then work your way up to the next city’s playgrounds, etc. If you need any more advice or live in the Western burbs and need a riding buddy, pm me.