As new as you can get

[BleeckerSt_Girl]

Hi, thank you for the welcomes. I'm sorry I didn't give more info before. I'm 29, and while I'm definitely not in the best shape of my life, I'm in fairly good shape, since I do other forms of exercising.

I hear you about getting comfortable before I pull my son in a trailer. That does make sense. We've got a nice, long walking/biking trail near my house that I'll be taking him on with a trailer before I ever go on the road with him.

Most excellent!

I'll not be buying a bike at Walmart, if I can help it. Fastdogs, my husband likes guns, and he has no problem paying lots of money for them, even though he actually only uses them a few times a year. I plan to use that as my bike buying angle.

Good plan. Plus, you can add the health angle for extra leverage!

I've been thinking about getting a hybrid. How would that do on longer rides? I know it wouldn't be as fast as a road bike, but I'm not too worried about speed. I know I'm all over the place with what I want, which does make it hard to give me advice.
I was looking at the website for a bike shop near me, at their hybrids, and they had some bikes starting at $269 and then up into the low $300's. Specifically, a Diamondback Kalamar, a Giant Cypress ST, and a Raleigh Detour 3.5. Are those bikes complete crap?

Hybrids are great all around bikes- they can do a lot- except maybe racing and triathlons, etc. Many people have happily ridden 100 mile rides on hybrids. Hybrids are (usually) less expensive than road bikes and are often more comfortable for new riders because you are sitting a little more upright. Also beginners really like the numbered gears on the hand grips, and they like the straight handlebars. An aluminum hybrid would be a good price and would be ideal for hauling a kid behind as well, and for putting racks on for shopping, etc. They can take very wide tires too, which gives a new rider added confidence. You can do a lot of long distance fun road riding on a hybrid. There is a lot of variety within the hybrid group- and I'd say you'd want to make it clear that you are not looking for a heavy 'comfort cruiser' type bike but rather more of a 'zippy' hybrid. Don't let some sales guy try to sell you a super heavy beginner's hybrid intended for riding only to the corner and back on flat terrain.
Many many people start with a hybrid and put thousands of miles on it, then decide to get a road bike for intense fast riding and voila!- they decide keep their beloved trusty hybrid for commuting or hauling kids and groceries.
If you do a lot of different kinds of riding it makes sense to have more than one kind of bike....but a hybrid is an excellent first bike choice for your situation, especially if as you say you are not too concerned with speed yet.

All this is just my own opinion.