The Improbable Bulk
Join Date: Jul 2005
Location: Wilkes-Barre, PA
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If you want integrated shifters, a price of $250 to $300 is going to be pretty challenging.
Integrated shifters alone cost a minimum of $150 new, and only rarely go used for under $100.
If you really want 27" wheels and integrated shifters, you will probably need to either get wheels custom built, or build your own (I had mine built). This is because the wheels with freehubs that accommodate the 8 cogs and higher needed for integrated shifters didn't come on 27" wheels. However, 700c wheels can work on many bikes that were designed for 27" wheels as long as the brakes can reach an additional 4mm.
In general, the shifters must match the type of cassette used (and must be compatible with the wheel). For example, an 8 speed Shimano shifter must use an 8 speed Shimano cassette. Campagnolo 9 speed shifters must go with a Campagnolo 9 speed cassette... (and so on).
The derailleurs are not typically as fussy (but there are exceptions) so any index capable Shimano rear derailleur will work with Shimano shifters, and any Campagnolo indexing derailleur will work with Campagnolo shifters.
Frames are personal taste, and if you like Schwinn, you will do fine, just as long as you get a bottom bracket that is compatible with the frame, and the crank used.
You will in some cases need special tools (or for one time installations, a trip to the bike shop to have them do the work) such as bottom bracket or headset installation.
For comparison... I bought a 1986 Schwinn Voyageur, and had a set of wheels built for it, and had it built by a shop with new Shimano 105 components. The cost of the upgrades (not counting the frame, saddle, handlebar/stem) was $850. If I had done it myself, I could have probably done it for about $500. I could have bought a similarly equipped new bike cheaper... which is the norm.
The unfortunate truth is that it is often cheaper to buy a bike than to build one, unless you find many of the used parts you need, and get good deals on them, and they are in great shape.