What kind of bike should I be looking for?

It sounds like you would like a "Comfort Bike". Comfort bikes, like the Electra Townie or the Diamondback Wildwood are great bikes for riding around town. They can have one or many gears, hand brakes, a super comfortable seat and they put the rider in an upright position. Many of the comfort bikes have suspension seat posts and adjustable stems to make the rider very comfortable. The Townie can be a bit more expensive than the Diamondback, but it is a nice bike. Let me know if you have any questions [email protected]

Yeah, they are called "hybrids" they are essentially a cross between a mountain and road bike. They are designed specially for commuters, are usually less expensive than road or mtn bikes, and are designed to be less stressful on the body (which also puts the rider in a safer position when riding in traffic). I would google them for more info, but you can usually find a good used hybrid for less than $300.

I would go to the swap meet and yard sales and buy a frame and parts and build a frankenbike. You can customize your Frankenbike to suit your needs for hardly any money at all. It will be fun to build and when someone asks you what kind of bike it is you can say its a Raleighschwinnhuffygiant or something like that.

Maybe you should look around for a single speed, 26" wheel, flat handlebar, spring loaded seat cruiser type bike? Also known as beach cruisers. Normally I wouldn't send anyone to a big box store for a bike. But in your case you might be able to find a usable bike in this genre from Huffy or Schwinn. They're not real complicated bikes. I would check it over to make sure the bolts on the wheels, stem, handlebar and seat are tight.

You could get a brand new hard-tail mountain bike for under $300 easy. I know Trek still makes the 820 for around $250, and most bike manuf. have similarly priced models too. Check out your local shops and see what they have in your range, ride a few around the block and see what feels best for you.

Breezer's line of transportation bikes are just what you have described, try googling them. They are ready when you are with lots of features like built in battery-free lights. They have a comfortable sitting design and handlebars at a perfect angle, not bent back. They also come ready with racks and fenders and lots of other stuff. They are very light, too, without needless thick tubing. The price is a little more than you estimated for the cheapest one, but few bikes for this purpose are under 300 dollars. If you bought one under 300 dollars, you would find yourself paying more for repairs, and add-ons that a Breezer already has.