You may or may not be able to bore it to 144 - apparently some of the CR's have a thin cylinder which prevents them from being bored to more than 134 or 139.
You will notice the difference regardless of whether its 134, 139 or 144. Apparently all 3 kits get near the same peak HP, but the 144 has more midrange and the 134 is more of a top end motor.
What do you mean by "keep up" with your 250? Speed is 95% rider, so YOU control how fast it's going on the track.
What you'll find is that a stock 125 is about 30-33 HP. Stock 250 2 strokes run in the mid 40s HP. A 144 that's been ported, high compression head for race gas, etc . . . will be in the 37-39 HP range. The best one I've seen on here was 39.6 HP on the dyno.
Given the weight difference between the 125 and the 250, a 144 is very quick, but it won't have nearly the low/mid of a 250.
Eric Gorr did my motor and I couldn't be happier with it. Depending on how much you like to rev it, you may find that you need to do top ends more often, but I haven't noticed much difference. Eric can give you the lowdown on all that.
http://www.ericgorr.com (site closed as he has it rebuilt). His phone number is floating around all over here if you run a search.
There is apparently very little extra stress on the motor resulting from the increased piston size because Eric's piston (which he designed for Wiseco) is only 1/2 ounce heavier than the stock 125 piston.
Try this link for my initial impressions after getting the motor dialed in:
http://www.dirtrider.net/forums3/showthread.php?t=126800
Most would say you're too heavy for a 125/134/144. However, read the last two posts in this thread:
http://www.dirtrider.net/forums3/showthread.php?t=124938
bclapham was racing at very hilly Glen Helen at 200+lbs and he liked the RM144 a lot. I'm sure others of that size would prefer a 450 4 stroke or maybe that new KTM 950. ;)