Welcome to AS. This thread will get more traffic in the chainsaw section. If you ask a moderator they can move it for you.
Personally I'd put the money for a 390 rebuild towards a better saw. Of course you could also throw a new top end on it and sell it on Craigslist. They seem to command a silly-high price around here.
Yes, an 044 is a great saw definitely worth rebuilding if it comes to that. Before it does though, I'd suggest replacing the rubber bits (fuel line and filter, impulse line, crank seals if needed) to avoid a meltdown in the first place.
I run a 20" bar on my be 440, but it's mostly a firewood saw. I know out west they'll slap some pretty long bars on a saw that size. I've got bigger saws with wrap handlebars though, so I use them for that job.