Have any of you pitched a directional or starting idea to bosses and have it go well? I feel like I'm at such a low "worked bee" level is have to send a lot of time preparing data to back up the idea. Also not sure if I should go to immediate boss who is cool but a little reserved about ideas like this or boss's boss who has more leverage to put an idea like this in action?

Tough to say... Do mgmt seem like reasonable people or is there a larger then needed barrier in between hierarchies? Ik you go to you boss's boss try to have a PoC on what the idea is. That's my idea though :p

I'm starting to think it's not the right time. Management is reasonable but new and I'm not sure how ambitious they want to be out the gate. Also there have been huge budget cuts and I just don't think anyone wants to think ahead right now, especially if it would require trying to hire. I slept for a couple hours after writing that rant and I'm even feeling less ambitious about it now.

I pitch ideas every so often. Just make sure you have a plan, pros/cons, and what the net result will be. Start off small. It helps to have a good track record before suggesting any big changes.