Lots of great responses. Here's the answers:
1) According to Sheldon Brown's calculator, I can go to a 42 or 44 tooth
> ring and the upper end will functionally be like a 53/14, and the bottom end
> at 39/23, which is workable. Will a 42 or 44 fit on the inner position and
> still clear the chainstay? I'm riding a Lemond Poprad.
Probably, but close. With an Octalink bracket, it's likely not an issue due
to stiffness.
1b) If not, what can I do? I suppose running on the outside might work.
> Is there a lateral adjustment on a 105 octalink bottom bracket?
One respondant reports having a better chainline outside. Pick whichever
works for the better chainline up the middle. One advocates for a square
taper setup just for this kind of adjustment. Another suggested an Octalink
track crank for best results.
2) I was told once that the reason you don't cross-gear is that it
> increases your chain wear and breakage. Running a single ring means I would
> definitely be running a combination that is cross-gearing. Should I worry?
> Is this hard on the chain or derailleur?
No and barely. The rear derailleur should be fine, and the chain needs
replacing anyway. Modern chains are build for a fair amount of abuse, so
this is unlikely to cause any additional pain.
3) Anything I didn't think of?
My big ring is too big for the riding I'm doing, and I should put on a 48 or
50. This completely makes sense now that I look at it. A 48t gives me all
the ratios I need for my commute, plus the bottom end I need for climbing on
the 39.
So....
Anyone out there have a 48t, 130BCD black FSA chainring they'd sell or trade
for a practically new 53t of same make? Thought I'd check before
ordering...
Thanks for all the info.
-Joel