It's very unlikely you'll lose just the one shoe, I'd expect both at the same time and possibly your pants too
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The trick with a commuting bike is to have a regular maintenance routine - clean the bike and lubricate the chain reasonably often - I try for weekly but depending on your mileage it can be less often. If doing lots of miles for commuting in bad weather then replace the gear and brake cables sometime in spring - if you do that you'll keep on top of it no problem.
When oiling the chain remember that less is more, put a tiny drop on each of the links one by one then turn the cranks a few times to get the oil worked into the chain and then wipe off the excess a couple of times - it should be reasonably dry to the touch afterwards. That will help stop the chain from getting too dirty or collecting grit and wearing out sooner.