The Lake Shore's OTP has actually improved rather dramatically recently. It's still somewhat iffy to rely on a long distance train for a connection like that as delays of course can and still do happen and in this case one also has to factor in the trek from South Station or Back Bay to North Station. But it's improved enough where I don't think it's "late for sure" nickname is still justified. It's among one of the better long distance trains for OTP these days.
Well, its OTP is good, except when it's not. After checking its recent history, I felt confident enough to book it for a family trip last October from ALB to BOS, connecting to the 10:30 p.m. Downeaster to Maine. I checked that morning, and it was only about 20 minutes late out of Cleveland, but by the time we arrived at the Rensselaer station, it had developed some mechanical problem and had only just cleared Buffalo. It lost more time all across New York and finally reached Albany about 8 p.m. and Boston at 1 a.m. Simply giving up and driving wasn't an option for us on this particular trip, so we had to scramble to find a last-minute hotel reservation in Boston, for which we paid dearly. So that, coupled with a similar experience the previous year, when we arrived BOS at 1:45 a.m., made me avoid the eastbound LSL this year.
If the proposal for a couple of additional BOS-ALB frequencies goes forward, I'm hoping there'll be an eastbound that arrives in Boston before 11 a.m. and another around 3 or 4 p.m. Westbound, the Lake Shore's 12:50 p.m. departure works OK, though a late afternoon departure would be better. Until then, we'll either drive to Wachusett or go eastbound via NYP.