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Yes, they're canti's. Agreed re. the permanent uphill...
The downtube shifters are friction. I will get this confirmed by a LBS, but I assume that this means that the rear mech will be able to shift the extra few millimetres for the greater number of cogs? Once more, I assume that they don't just push the cogs closer together (?!)
I may take you up on the aria drum brake. I will seek to use the existing drum though because it's not worn and the drum to frame spacing (for the attachment) is likely to be irregular.
A2theJ
gbj_tester
Changing wheel size will have implications on your brakes though (are they canti's?) Also you don't want a smaller wheel on the back than the front because no.
I suspect you can quite easily upgrade to more gears. I see downtube shifters, are they friction or indexed? If the former then it should work straight away with a new cassette and rear derailleur. Otherwise it might be worth updating the shifters to indexed 8 speed or higher.
If you do go for a new rear hub and need a new drum, I have an arai drum brake sitting in the cupboard that would like a new home.