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If you really like the steel frame, Id say keep it/store it and build up a lightweight bike.
In my experience I always come crawling back to steel but it is nice to try different setups.
Weightwise I never really notice that much, its the modern bikes handling/position and the different gear ratios that I notice the most.
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I’d say completely depends on your riding.
In my case I’m very militant about watching for glass, avoiding certain roads that I know are filled with late night bars (glass) and staying more on the road then cycle lane, I find there’s a a lot more puncturey debris the closer you get the the sidewalk.Tires wise I use Schwable duranos which I’d rate.
Also late to the party! Been on here for a few years and would pay membership annually