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What issues could crop up?
You might get more help over at the tandems thread
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Is it a sensible idea to replace these wheels with modern 26” size?
Probably not. 26×1⅜ is 590, so the best way to modernise would probably be 650B, i.e. 584. Common 26" (i.e. MTB) rims are 559, which is a much bigger change and will probably make it almost impossible to find brakes given that you already have a pretty long drop with the 590 rims.
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Also has an old clip type headset, the quill stem that is currently installed seems a lot more modern and is very hard / impossible to do up tightly, as in you can force it to shift out of place if you hold the wheel still. Are there different internal steerer diameters but still ‘1inch’ (particularly for old bikes)?
Clip type stems on single bikes are ~22mm diameter quill, not 22.2mm like usual. The pinch bolt in the clip holds it in afaik and there’s no wedge or expander. I’ve got a 70s French Atax stem in my Parkes which fits in because it’s 22mm. It’s secured by the expander but I haven’t tried pulling it around while done up.
I -think- there is a slightly bigger diameter clip for tandems and I wonder if yours might be. Could well be that a 22.2 is loose in there and the wedge doesn’t really pull it up. Could also be worn quill or the steerer reamed to fit a normal quill but done a bit too much. Wonder if it’s worth putting a spare set of bars in another quill and seeing if it makes a difference. If you’re anywhere near Staines you’re welcome to borrow some of mine.
Fixing up a tandem I bought during summer (for cheapz, £20 and went halfs with someone)
It rides as it is but I want to make it solid more comfortable and safer!
Has 26 x 1 3/8 wheels, caliper rim brakes and rear drum brake operated by stoker. The drum brake looks like it’s beyond saving. Is it a sensible idea to replace these wheels with modern 26” size? What issues could crop up? I’d lose the drum brake of course.
Also has an old clip type headset, the quill stem that is currently installed seems a lot more modern and is very hard / impossible to do up tightly, as in you can force it to shift out of place if you hold the wheel still. Are there different internal steerer diameters but still ‘1inch’ (particularly for old bikes)?
The bikes at a friends house but will post some more pictures soon