"Michael S. Moorhead" wrote in message
...

A friend and I have been taking longer and longer weekend rides on our
hybrid and mountain bikes and have been contemplating buying used road
bikes
during the off-season.

When is the best time of year and where should we be looking for used
bikes?

Garage sale time is a pretty good time, if you are looking for something
modest.
There's a bunch of things to look for; Jon Isaacs has a writeup he will send
on request giving a lot of tips about looking for a used bike (search up his
e-mail address using Google on this newsgroup.)

Beyond size, the main thing to look for is wheels. If they are steel, you
will need to get the bike very cheaply, because you are probably going to
want to replace those steel rims with aluminum alloy wheels, and that will
be about $130+.
That's not necessarily bad (because a bike with new wheels is a good thing),
but something you should prepare for.
Also, you should know that 27 inch wheels are an obsolete size; you can
still get replacement parts, but there are no new ones made (700mm replaced
it).

How old is old? Does quality fade off dramatically after 5 years or so?

Not really quality. The two road bikes I have were made in 1976 and 1980.
HOWEVER, newer bikes will have better shifting (e.g. STI rather than those
downtube friction shifters).
If you grew up with friction shifters, these are OK, but if you really like
the grip-shift type of shifting on modern hybrids and mountain bikes, you
will find friction shifting an adjustment.

About what could one ask for ~$300?

You can certainly get a moderate original quality road bike you can put
thousands of miles on, if you are patient.
However, it may be wise to look for something in the ~$200 range, with the
idea of spending ~$100 overhauling the bearings, replacing some of the
rubber parts, and just generally getting it in tune.

When I returned to riding a road bike, I bought one for $40 at a rummage
sale -- then spent $40 on an upgraded saddle, and $140 for new wheels and
$40 for one new tire and new tubes. So, the $40 bike cost $260 to get
outfitted -- on the other hand I now have over 7000 miles on this bike.

Some of the best garage sale values are bikes that have not been ridden in a
decade or more, and the owner just wants the garage space back. However, 10
year old tires that have been sitting in a garage are not tires you will
want, and bearings that haven't moved in 10 years will greatly benefit from
cleaning and new grease.

None of this contradicts what the other posters said; there was good advice
there, also.