If you are getting paid, they aren't hobbies. They are jobs.

Software, with the piracy available, good luck selling it. Unless it's stuff that is hardware dongle protected (like Pro Tools and their iLok) it can be had for free. The higher end computers should go quickly on Craigslist type outlets. You may have something specific to your area as well.

Best advice for someone in this place in their musical life if to make sure you are REALLY done with it. I retired from it once and sold almost all my gear and have been rebuying every since despite the fact that I barely write or play anymore. (To wit: The used Kurzweil I just bought. And am now tearing my hair out learning to use it. Though when I CAN figure something out on that manual written in Kurzweilese it is quite rewarding.)

The guitars are being sold off though. 3 are gone, 3 are on consignment right now.

The thing with selling computers is that they tend to not travel well, so you will probably be dealing mainly with local sales. The downside of that is that it needs to be crystal clear, possibly even in writing, that the sale doesn't include lifetime free tech support on them. I have run into that. Fortunately I have the attitude where I can tell people that whatever problem they are having, THEY are having and to stop bothering me.