My advice you need to plan. $ how much can you stretch too. Are you doing the work that will halve the price. Or some of the work pro rata. Leak back tests, compression tests. Oil pressure. these will determine a lot. If the head comes off then crank can be assessed. With bigger bores and cams etc you should be able to get a lot of power out of your bike. As said you can get near 100cube boring out your 88. I f you want a square motor you are as close to 4 x4 as you can get!
I like the 88" stroke with barrels bored to 95" , they rev smooth. but depends what your planing to use the bike for?
Thanks Milo, yes it definitely needs a top end and cams.