to the OP, sounds like the most stable minded plan i've seen on this forum in a while.
Most flatwater "newbs" jump right from the 440 to a souped up flatwater competition boat and then try to learn. I'm a big follower of the learn the basics and gain some knowledge along the way before progressing to flips, rolls, etc.
Ride the hell out of that square and find another hull to build up (squarenose/roundnose) Build a mild limited 701-771 with 62Tcases/61X ported cylinder, High compression head, (MSD enhancer, epic, or total loss) with stock 38's and a b pipe and ride some more.
When all that gets old in a couple years, jump on someone else's lightweight/big power setup. If that seems like its for you once you progress your skillset, then sell everything you got and buy one of them.
Good luck and keep riding!