What Kind of Bike Is Appropriate For A Newbie-ish Rider?

Take the free bike unless it is terrible to ride. Then see how much you ride. I tend to buy bikes second hand because you can get them much more cheaply than new because many people buy bikes the same way people join gyms. They go out and buy a fancy bike and then don't ride it. Don't fall into that trap.

At the advice of a serious cycling friend, I bought a cheap bike first. About $100 at Sprawlmart. But I outgrew it pretty fast on a couple of long, leisurely rides, which I take for mostly social purposes about once every couple of months. Fourteen miles or so, usually, and the cheap bike just completely beat me up on those. So I upgraded pretty quickly to a used Townie, which I'm totally in love with. I would agree that you should start with the free one, but don't be afraid to upgrade as soon as you feel the need. The higher quality of my second bike made all the difference in the world to me. I use mine mostly for running errands and short (about an hour) pleasure rides around town.

a 70's cruiser usually has a good amount of room for the seat to move up, it's the short people who often can't fit on them easily. if it's an internally geared three speed, you may need to put oil in the rear hub but that's not super difficult to do and most stuff is googlable, or search bikeforums. if you have any questions when you get it, feel free to memail me, mr pht and i run a bike rehab/used bike business so he's seen many, many vintage cruisers, and no question will be dumb because i literally knew not a thing about bikes a few years ago and have asked so, so many dumb questions.

You haven't told us whether you live in a flat or hilly place. It makes a difference.

I kind of agree with wierdo. Cheap is great and free is even better, but heavy bikes suck, and heavy tyres and wheels are worse. They just suck the fun out of riding. Obviously you don't want to spend too much, and you aren't sure how much you'll use it, but I figure you're more likely to ride more when riding is fun and takes less effort. In a week or two you'll feel just as stable on the hybrid, but you'll be going faster with less effort. Frankly the most important thing for new riders is finding a shop that you like with people you are happy to deal with and ask questions of.

Tested the vintage bike - when she said vintage, she meant it: no handbrakes. You brake by pedaling backwards. This...might be too much for me given my relative inexperience with bikes. So now I'm kinda leaning towards the comfort bike, knowing full well that I might grow out of it rather quickly. Scoured CL for more used bike options, but feeling a bit overwhelmed now. Sigh.

I'm going to break with the pack here and say that it can be demoralizing to have a super-heavy bike if you're not always riding on flat ground. IMO, the lighter the better. Also, you want lots of gears if your town is at all hilly. Constantly being in too high a gear is a great way to ruin your knees. You can get a reasonably decent reasonably light chinese hybrid for $400 new. You want something like that, only a couple of years old. The good and bad thing about the cruisers is the very comfortable riding position. Problem is that it's terribly inefficient. There's a reason why people don't ride upright on road bikes. My SO has http://www.giant-bicycles.com/en-us/bikes/model/cypress.st.w/9051/48945/, but with only 6 gears, and it would probably be fine if it didn't weigh 50 pounds or whatever it is that it weighs, but since it does, the gearing isn't nearly low enough. Looks great, though. Most of Tulsa isn't that hilly, but it's still not a great bike for this terrain. To use a personal example, my SO and I bought our bikes at the same time and within a month I was riding a hundred miles a week because it was fun. Only the steepest hills were any real trouble for me. She, on the other hand, rode hers once a week at best because even the mild hills on the trails near where we lived at the time were very uncomfortable with a heavy bike lacking gears.

And here, if you're looking for what a typical 70's women's cruiser looks like, here's some we sold: http://www.flickr.com/photos/phatmike/6332388161/in/set-72157627973554587 http://www.flickr.com/photos/phatmike/6332388149/in/set-72157627973554587/ http://www.flickr.com/photos/phatmike/5912360827/in/set-72157627973554587/ All these guys are heavy, but fun to ride unless you're going up a steep hill. And the ten-speed was good for having an easier uphill gear.

ON rereading, you're not looking to commute. Go for a simple, second-hand mountain bike then. If a cruiser is what I think it is, you won't have any fun at all when the trail goes uphill.