Upload & Sell: Off
'I think one of the hard parts is acknowledging what is actually a NEED vs a WANT.'
1. Have you used the item in the last 6-12 months?
2. Do you have a clear and present NEED for an item, or an anticipated need in the next 12 months?
If 'no' to both, sell.
Reverse the process for buying.
I'd have to agree here. I recall my early days of digital, picking up all sorts of lenses and trying all sorts of things, trying to make everything work, never really understanding why. For years now, I've just stuck with what will actually serve a purpose and I'll use. Sure, there is a process of trying "stuff" and finding what you like, but after a while you can make a well educated guess at things, and just go with it, or stick with what you have that you like, shed the unused stuff.
Just to play mind games, I think it's important to realise that WANTS and NEEDS are the same thing in this situation. You don't NEED any photographic item in my mind. Some will be more USEFUL in achieving the objective if you work around the limitations. Whatever you use, it will have limitations, even if you carry everything you own. So find the most USEFUL and learn how to get the most out of it, learn how you want to use it... Not someone else. As touched upon, using some appropriate and sticking with it, consistently, for 6-12 months is very productive in my opinion.
Not to be "anti gear" as I enjoy the discussions on here (obviously) but I feel if you stick with some equipment for a good period of time you realise the greater tool will always be your mind.