Must agree with Paul here regarding a track pump, much less effort to get up to 100psi+, money well spent.  Also, spend as much as you can on tyres, I'm running Schwalbe Ultremo ZX on the roadie, although I did have a puncture last week, own fault for riding in the dark!  I've also got Schwalbe on the MTB, running tubeless, not cheap but you get what you pay for.  As regards club rides, more of a social rider myself, depends on the mood at the time, although living on the IoM there are some serious riders out and about at times!  Why not try a Sportive, 100km is a great target to work towards?