Kind of long post...I'm rambling and detailing things as I think this through...sorry
I have a chromo Masi frame with lugged steel fork that I bought several years ago. Bought it as a singlespeed and I've since converted to a geared bike (2010 Masi Speciale Commuter). I have four bikes, all of them more expensive than this one, but I love how this bike rides. The fit is perfect. I can go from weeks of riding seldomly, and then do a 4-day tour and walk off the bike each day with a smile on my face.
I ride mix of paved and gravel roads (not bad gravel). I'm still running the stock 32mm Kenda tires and vary psi depending on ride.
So it feels 'odd' spending money on a bike that cost me less than $500. Granted, I've sinced added parts that I used for the build (my first build). That said, I now have most of the parts I want, and there are a few where I'm wondering if I should upgrade...or just leave as is. You know how this goes, it's the 'spending bug' and buying nice new stuff that gets you

but I don't mind adding to this bike
Here is what I'm not planning on changing:
- frame/fork
- Brooks B17
- handlebars
- wheels (handbuilt A719 / 105 hubs)
Here is what I'm changing in the next week:
- mushie dia-compe brake calipers to Tektro r559
- new brake cables/housing
- new bar tape (my fav - Lizard Skins 3.2mm)
What I added when converted to geared bike:
- Dura Ace downtube shifters, love them in the winter when it's freezing out and I've got bulky gloves, actually I just love DT shifters (first time with them...and I'm under 40...woud've thought)
- 105 RD and FD (triple)
- Tiagra crank
And what is unchanged:
- seat post (8 year old carbon OEM post on a Giant bike that I've had on there since I bought the bike)
- stock Ritchey head set
- stock Ritchey stem
Possible upgrades:
- either a newer carbon fibre seatpost if I can remain convinced it helps with comfort, otherwise I want something that's solid and with decent set-back for the B17 (darn short rails). Would go with a Thomson post but straight wont work and there isn't enough room for their set-back post. Maybe a VO grand cru?
- new headset and/or stem (ones on there are fine, but a chris king would look nice...I have one on another bike but it's one of those parts that have bling, while being rock solid, but is hard to question the $ when the one I have seems fine). Stem is a 4-bolt and is also fine...and I wouldn't want to change the length/angle
- the drive train, while relatively new and working fine, was acquired in pieces (all new) for good prices. When I decided to go for a triple (9-sp), it was 'because' I got the pieces for a good deal. I could've saved weight with a double/compact, but it cost more and wasn't sure if I wanted the triple for touring (not actually doing much touring in any case). Also, I didn't realize that there are not a lot of triple cranks out there...hence the Tiagra (but I don't want to change the DT shifters)
- brake levers (the one component that was pour from the start were the brakes...will be putting on the r559 and if they improve overall braking, then I'm probably keeping with the tektro levers)
- cages (got some $2 ones on there 4ever)
- tires (was just going to replace with another 32mm tire when these are done)
Would you spend? Where would you spend? Have you had a bike this that started off relatively cheap and you spent money on it...thoughts afterwards (would you do it again)???
Thanks so much for reading my rambling...