I have the same GPS and it’s basically a new job, in your words, even with the 355, which is the route I’m taking.
As I posted elsewhere I started looking at replacing the 300XL since it’s getting very long in the tooth, although it’s working perfectly well. It’s not even close to a slide-in replacement, unfortunately.
Aside from questions about antennae and coax (the 300XL isn’t WAAS), the indicator needs to be replaced as well. “Basic” ones are $3K, so I looked at an Aspen. Then a G5. Then a GI 275. Then two 275s, so they can drive my Piper AP and I can dump the vac system. That’s where I am now.
There’s no cheap way to move past the 300XL that I’ve found. That said, I had a Garmin 396 in the panel, fed by the 300XL since 2008 and it was great. Even better now that I swapped an Aera 660 for the 396. And a GDL50 on the dash for traffic, weather, and AHARS on the 660.
So depending on your goals, you may consider keeping the 300XL and making it a “color moving map” with a 660 and GDL50.