I can relate to the OP.
I have a little bit more than 100, and only about 1/3 of it is brush and trees now- when it started out 90% brush and trees.
I stared with cheap **** saws (poulan, craftsman, homelite) borrowed saws (husq rancher, stihl 038 AV, echo CS590, etc), bought an MS170, which soon became a MS361, fast forward, I now have 3x MS361 and an MS461, HT131 and either an MS261 or 241 on the way soon.
No regrets.
However, with the reputation for the XP series (similar amount of fan boys to th pro-stihl saws), I don't think you'd regret a 346xp or 550xp- I use my 76.5cc saw the most for felling and bucking, and the 60cc's are set up with different chain combinations.
One wears RM for dirty wood, one wears RS for clean wood, one has a long bar with semi skip- they are overkill for light work and that's why I'm looking at saws in the same class as you now.
I know it's heresy and the brand loyalists will be pissed, but if a good deal pops up on a 45-50cc XP I will probably snatch it up. Hopefully chuck won't be too pissed at me.