Because as my Bike Butler will tell you once you start cranking out the miles and my mileage is high by most people's standards but stupidly small compared to Steve's, bike maintainance becomes seriously high.
not really, I've found if you run everything together, it all wears the same, so if your not always changing out cassettes/chains/rings when checkers tell you they are worn then they go on for a long time, i recently changed from 10 speed SRAM Red to 11 Speed Dura Ace - the Red had done 14,000km on the same rings/cassette/chain/cables/bb30 bearings including through winter, barely maintained other than a wipe down and an oil for the chain
ok 14,000km in the scheme of things is 6 weeks riding for Steve, but I'm a believer that if you tinker too much you can cause yourself greater wear and increased cost
essentially though in steves position, considering you can get a complete Ultegra grouspet for sub 400 and 105 for sub 300, id just be replacing the lot once a month, with 3 bikes in circulation, it should be easy enough to always have a "new" bike ready to go, although of course it being 100+ miles away yesterday didn't help, it does throw up the question of shorter more repetitive local loops so he's never far from help, either that or have the 3 bikes all ready to go strategically placed in high mileage areas