Ok, i realize the decision of whether to sink $$$ into an older bike (and just how much $$ to sink) is highly personal, but any opinions would be appreciated for my scenario.

I have a 1986 Trek 500 "Tri-Series" - a misnomer, as it has 'sports' geometry - not a total lame pig ride but not as aggressive as modern performance bikes either. It has a 531 main triangle, tange straight gauge stays and fork. 12 speed (6 speed rear) and the old style brakes with exposed cables. Very nice condition, just a few paint chips and had all the original parts except for toe clip straps; the tires and bar tape were shot. It fits me okay, I like a lot of standover clearance, which this has, with a decent top tube length for such a small bike (it is a 18" with 53cm TT. Most bikes that size I've seen are 50cm or so TT). I need to replace the 70mm stock stem with a 100 or 110 and the 38cm handle bar with something wider.

I also have a newer AL bike (2002) with Dura Ace 9 spd. I was hoping to keep the Trek as a rainy day/winter/loaner. I have a mountain bike I use as a commuter but figured the Trek would be good as a backup for that as well. I plan to do lots of 50-100 mile rides, maybe try some Cat 5 races. I reckoned the newer bike would last longer for racing if I thrashed the Trek on at leats 50-75% of training and touring rides.

I paid $200 for the Trek about 6 months ago, mostly purchased because:

a) I wanted a 'new' road bike and figured I'd try a more affordable old one first to make sure I liked the position, feel, etc - I am more used to flat bars and mtbs. I liked it a lot and bought the 2002 a few months later.

b) I missed my old 1981 Miyata 110 steel road bike, with relaxed geometry and all day comfort. Used that bike for commutes, half centuries, etc and loved the ride.

The Trek has not disappointed in replacing the Miyata's vintage silky ride. I did a thirty mile half metric century the other day and it rode smoothly and comfortably, even witha sore neck I'd suffered from a pinched nerve the day before. It responded just fine to standing climbs, accelerations, etc. It does however feel clunky next to the new bike in terms of the downtube shifting, brake lever set up, etc. Seated climbs are sluggish - the bike weighs 23-24 lbs. The brakes are rather low end shimano single pivot calipers - even if I slap on decent aero bar brake levers, I don't know how much the modulation would improve with the same calipers.

I started buying bits and pieces to upgrade sensibly - new tires and bar tape, clipless peds, my preferred model of saddle, wider handlebar etc. I figured i could live with brakes as is - They do stop safely enough, it's just harder on the hands than the smooth feel I am used to on newer bikes.

Then I noticed the chainwheels are bent, so I'd need another $40 or so for a new set, which made me wonder whether I was crossing the line in terms of upgrading wisdom. Now it turns out the rear axle is bent - not enough to make the bike unridable, but I know it's there (you feel it when coasting at speed) and it bugs me to ride a bike like that. I am the type who prefers to fix such things, even on a beater or hack bike.

Now I am looking at the entire list of upgrades done and left to do and tallying them, to decide if I should go on or just sell this bike and stick with my 2002 racer, and look towards a newer bike in the next few years; here's my choices as I see them:

1. sell it with all the original parts and hope to get my $200 back before I blow any more money - My wife likes that one!! we are already tripping over the 5 bikes in our 1-bedroom apt!

2. try to cheaply fix it - this will still hover near $500 in parts by the time I am done, and I still will have lackluster brakes and downtube shifters-not knocking these but I have never liked them. My miyata was cheap and had setm shifters, which I replaced with bar mtb shifters. I know this solution might make the most sense financially but I actually like it the least - like many other mad scientist frankensteiners, I prefer to fix things nicely.

3. go whole hog and upgrade the bike with a 9 spd wheel and cassette, new chain - that's about 150ish right there - or even add brifters and new brake calipers for another 250ish. This will make the bike quite nice but at a total investment of almost $1000!

4. strip it down to a fixed gear - it has 165mm cranks and horizontal rear dropouts. This would be cheap; I could do all the work myself, and the dearilleurs etc. could be sold to pay for a track rear wheel and chain. The Negatives with this route are at 41, my knees are so-so and I wouldn't use it on anything but short rides. I love fixies but I sold all mine a few years back and haven't missed them from a practical standpoint.

I know these decisions are all about what each person's gut tells them to do, but I am really torn. I know it's silly to spend a lot on a steel bike that's 20 years old with a 1" threaded front end.....on the other hand, would my shiny 3 yr old AL bike still be around in another 17 years? If not, why is it not silly to dump thousands into that one?


Any thoughts would be great.