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Hi,
I would recommend clipless (I have used Shimano m520 on all my bikes for years now, they're ultra reliable and cheap) with MTB shoes, i.e. something you can put your foot down in and not be slipping all over the place/occasional walking. You could also benefit from some waterproof overshoes for the wet days, and if you're feeling really keen - gaiters.
Just some ideas anyway.
Your spiffing condor shoes would need road cleats specific to the type of clipless pedals you were using. New pedals come with the appropriate cleats included.
Obviously this would mean investing in new/ 'new old' stuff, but we all like that, don't we?
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I recently built up a Caad10 with fairly nice parts, however I'm thinking of dismantling and selling it as I still prefer riding the Pompino I've had for 10 years. The 'dale feels dead in comparison, making me wonder how nice a 'good' steel frame would ride.
Also, after so long on a SS, gears just seem like a complete PITA, anyone else have these thoughts?
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user49596 - That's a nice looking Pomp, also those Autumn leaves look uskomaton.