If I were you, I would simply widen the intake and exhaust a mm or two on each side(make sure to wait until you get a new piston in to check the clearances, tho). I'd remove the ridge on the lower transfers, but leave the rest of the timing alone unless you wanna bring the uppers up to where they should be without a gasket. That's another mm or so, and she should be a good runner. The timing on the exhaust and intake on these saws are spot on for a ported work saw, so I wouldn't mod them. Advance the timing .020 on that new crank and it should give you 35-38* overall advance for a nice burn. We have quality fuel in the UK and Ireland, so I wouldn't worry bout detonation. Hell, I saw 102 and 98 octane at the pumps in places in the UK. 95 is our minimum here. And, personally, I think you get far more torque from good ignition advance than good squish here. On a chainsaw, that magical .020 squish 'efficiency' isn't as important as the timing is compared to sumfin like,say, a 125 or 250cc motorbike. Most of the year the air here is cool and dense, too. So timing is where it's at for us.
Also, since you'll have her apart, may as well look at other rebuild and upgrade threads to see if there are some easy tweaks to chunk in to her.
I would also get an aftermarket exhaust, a cheap-o chinese one without a baffle.
Some folks say the baffle adds torque, but no one has really proven it's a big difference in wood. What I do know is it causes the exhaust to heat up more right where you need it the least - at the exhaust port. And if there is any carbon build up or burnt sawdust on that side of the engine, it can cause it to shoot back in to the engine, or grind up against the piston. And carbon is very hard. I have seen many saws with baffles right at the exhaust that have damage to that side of the piston, but the intake side is perfect. So, in my mind, it's worth it for longevity not to have a baffle.
This is an aftermarket one I use that I've opened up a bit. 8 bucks:
I haven't touched my 044 myself yet - it's freezing and wet out and my hands are shaking too much. I need a diesel heater since the shed isn't plumbed for electricity. Blah.