I have gone through a similar thought process as well with various hobbies over the years.
Consider moving slowly. First, don't do anything for a few months. Think about it. Maybe do some garage reorganization, as you mentioned. Next, if you still want to move forward, maybe sell one of the least used/loved pieces (a tall order I know!). See how that feels; maybe wait a month or two. If was painless, sell another, and so on until you reach a point at which you are comfortable with what you have.
The best part of selling too much off is that you'll have to replace it! :greenchainsaw:
Very good advice.
An update: Started tackling the garage clutter last night. Dragged everything out of the garage, built a bunch of new shelves. Rearranged where I park the wheeled OPE and hung the trimmers and blowers on the wall and from the rafters. Got some floor space back. Started going through everything else tonight, freecycled off a ton of stuff (including trimmers, mowers, and a couple saw projects that I know I can live without) and threw out a good bit more crap. Gave away a bunch of gas cans of different sizes and types, which took up a ton of floor space; I'm gonna replace them with more space-efficient Scepter jerry cans. So far I have twice as much floor space as I had two days ago. I'm feeling so much better already, so I think the root of my frustration was the clutter even more than I thought it was.
Still hoping to sell off a few things to roll the proceeds into a splitter if I can carve out enough floorspace in the reorganized garage, but I think that most of the remaining saws are safe for now.