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You should keep your 18's in case you ever sell/trade it.
You can get away with all seasons in Boston - I use my 19"s for this (have 21's for the summer). The issue is tire width, stopping distance and road quality. You'll probably find it a little slippery with 20's when it is cold and slushy.
Although it's a little work to switch, as long as they are already mounted, it really isn't much work or cost to switch winter/summer.
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2012 F10 550xi Carbon black/oyster
2011 E92 M3 SSII/black
2012 W166 ML63 Steel grey/porcelain
2007 E93 monaco blue/beige (retired)
2010 E70 35d Space grey/saddle brown (retired)
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