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You can do this.
Buy a Glenn's. Read the chapter inside on what tools you need. Look on Amazon for tools, if you buy a bunch at the same time shipping charges are combined with most shippers. I'm a big fan of Niagara's storefront on Amazon. Or you can shop at your LBS for tools.
Find out what you need for your particular bike(s) as certain tools are quite specific to types of components and brands. Things like freewheel removers and bottom bracket wrenches will need to be the correct type and configuration to match the component on your particular bike. Other tools one will need are things like a work stand, open-end wrench set, cone wrenches, a chain tool, pedal wrench, crank puller, spoke wrench. Screwdrivers -and things like that. Don't forget a tool box to keep your bike tools together and safe.
For bike-specific tools it is best to stick with the better names -Park & Pedro's. But some of the Avenir, and other lower-end tools aren't too bad and can be much cheaper to purchase. A nice thing about Amazon is the customer reviews. Read and pay attention to them regarding the bike tools. Average the reviews over a range if there are a number of them. Some people give bad reviews to good tools because they are ignorant and some people give good reviews to bad tools for the same reason.
For general tools such as wrenches, pliers and screwdrivers just about anything will do. Bicycles are so light-duty that heavy-duty high-end tools are not really necessary. I've been a professional wrench-turner for nearly my entire life and I appreciate nice tools but they really aren't necessary for a home mechanic working on a bicycle. Harbor Freight makes some decent tools at very low purchase prices. Craftsman tools aren't what they used to be but the cost has fallen on them as well and Kmart is still honoring the Sears return policy now that that they own the company. As far as quality I don't think that that Harbor Freight is much behind the Craftsman tools these days. It's regression to the mean here as most of these tools are made in the same factories in China anyhow. Or one can go to a place like Menards and save big money on pretty much the same tools over there. There is a nice metric open-end wrench set at menards for $3.99 that is sometimes on sale for $2.99.
Then, after one gets set up and spends a few hundred on tools and materials just DO it. Push one's self out of the comfort envelope and try your own hand. The Glenn's book pretty much walks you through every minor and major repair task with good explanations and pictures.
If you get over your head then ask for help. There are a ton of helpful people on this list who would be happy to give advice or even come over and bail you out. If worst comes to worst you can always haul the bike into the LBS to put things back together for you. Bikes are light and are easy to carry. Put all the parts into a box and swallow your pride and go in. They will not laugh at you and if they do then find another LBS that doesn't pull such silly behavior on their customers. Anyone can work on a bike with a little bit of gumption and a few special tools. It really doesn't take much as bicycles are simple machines and really not that complicated.
One last thing -Read every single page on Sheldon's site. The guy was a font of information on bikes.
+1 on Sheldon and the Park Tools videos. Another great resource is the Mechanics forum at BikeForums.net.
Also you might want to consider getting an inexpensive spare bike to practice on, if you don't have one already. Or to ride while you are working on your daily rider. Being under the gun to get something fixed in a hurry can be super frustrating. And in the peak of the summer riding season your LBS might take a few days or week to do that repair anyway.
If your spare(s) are of similar vintage, you can also sometimes cannibalize the spare bike(s) for parts and then replace them later at your leisure from the parts bins at Working Bikes, or via the Chainlink Marketplace, Craigslist etc, rather than needing to buy new parts all the time.
+1 on a spare bike. Getting a spare bike (even it if is a single-speed cruiser from the 80's) and learning to tear it down, clean/degrease, rebuild with fresh bearings and fixing up any minor issues to make it into a runner again will not only give you a lot of experience at low risk -but in the end you'll have a spare bike to ride when your main bike is taken apart.
I just can't imagine only having one bike. 3 is absolute minimum I can bear to own.
+1 on waiting for parts. Even if you buy parts from your LBS instead of online they will probably have to order something themselves that they don't stock sooner or later. A portion of working on bikes is waiting on parts.
+1 on using used parts and combining bikes to make one good one.
Be aware that as the sickness takes hold the home-mechanic will start to amass a huge array of spare parts and such. After a while one will realize that THIS BIT will be useful in the future and quite costly to buy new. It's best to save it in a box with the rest of your stuff for a rainy day.
Handlebars, headset parts, Tires, tubes, wheels...
Yes, it can be a sickness -but an oh so enjoyable one.
+1 on niagra via amazon.
+1 on sheldon brown (RIP)
REI Lincoln Park's Advanced Bike Maint. Course begins tonight. As of right now we still have one space available.
http://www.rei.com/event/28361/session/34969
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