Re: Getting into Biking
-narrow seats It doesn't take long to get used to it - 2 or 3 weeks of riding at the most.
-good bikes: The key is fit. Very important to get one that fits appropriately. There is no substitute for a good local bike shop here. They will be able to help you pick the right size bike and get it adjusted appropriately so that you ride comfortably. Many shops offer fitting on bikes bought from them or sell a custom fit service which can be helpful if you buy your bike online. You can do a pretty good fit if you are minorly mechanically inclined and pull some info of the net.
Unfortunately, LBS's are rarely the cheapest place to buy bikes. However, aside from fitting services, most will give you free tuneups on your bike and some will even allow you to trade-up bikes bought from them when you are ready for a better bike. Some of the discount bike shops(got a performance bike shop near you?) offer good prices on bikes and usually have a house brand that are decent.
After fit, your component group is important. Frame differences are negligible other than material - almost all bikes in your range are either aluminum or aluminum/carbon, with most being aluminum. Ask whoever you shop with the differences in component levels. You'll mostly be dealing with shimano and they have >4 levels of components, from crap to pro racer quality.
There's some good deals online on bikes, including on ebay. Check in the back of Bicycling magazine for online retailers. A couple of the older bike names (mercier for example) were bought and someone is buying spec bikes from Asia(where most bikes are made) and putting their stickers on them. Some of these bikes come with pretty decent component groups and are a good value.
This spring I bought a '05 leftover Scattante (Performance bike's house brand), aluminum and carbon frame, carbon fork, truvativ cranks, and full ultegra for less than $750. A comparatively equipped bike will run about $1.5k-$2k, so there are good values out there if you look for them.
Don't forget the accessories you'll need - helmet, shorts, gloves, water bottles, shoes, tire patch kit, etc when figuring how much you can spend.
If you want to go the used route - and there is really nothing wrong with that - ask at bike shops and find your local bike club and triathlon training club. People are always looking to move up and finding a good used bike is not hard. The club I ride with has at least one member who is always buying and selling bikes. Often a couple year old used bike that cost $1k is as good as a new bike that costs $2k.
-20 miles is nothing on a bike. You should be able to do that after a couple of weeks of riding if you are not a complete tub of goo now. The program is to ride. That's all it takes to get there. Finding someone to ride with will help you get stronger, faster, and more endurance in less time than you will riding alone. LBS's will often have group rides and cycling clubs are a good way to go. Cycling clubs will have a full range of rides for all level riders and usually there's a bit of friendly competition involved...town line sprints, racing to see who can get to the top of a hill first, and the like. All will make you a stronger rider.
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