What I'd upgrade equipment-wise if I had my druthers:
360 Cameras
Ricoh Theta Z1: most 360 cameras are built for action video and make photography an afterthought. The Z1 is a photography first tool with the largest sensor, raw image file options and a quality of image quality rather than quantitity. It's expensive, but if you're into 360 photography and especially exploring the edges of it, the Z1 is the tool.
GoPro Max 360 Camera: I've chewed up a few Thetas doing action photography. The GoPro Max is pretty much everything proof and produces quality 360 images, though it is (like most 360 cameras) video focused.
At 16.6 mega-pixels the Max produces nice images, and the time lapse photography option would work well for on-bike photography.
It'd be nice to have an on-bike camera that I could just leave filming when the rains come. I currently have to get the dainty Theta out of the way whenever the weather sets in.
Aerial/Drone Photography
DJI Mini 2: I've got a Phantom 2 and it's a fine thing, but it's big and increasing restrictions on drone flight make it more and more difficult to fly. You can get around most of that by flying a micro drone (under 250 grams), which don't require the same restrictions.
There are super cheap options with poor cameras and disposable air-frames, but the Mini-2 borrows the best tech from its big brothers in a small, foldable package that travels well.
Digital SLR Camera Updates
Canon 6D Mk2 SLR camera body: I'm still enjoying my Canon Rebel T6i and I'd want an more advanced camera body that would still let me use the lenses I'm familiar with. The 6D is the next step on from the entry level Rebel cameras with improved features and range. Stepping up doesn't come cheap though, though it would still be able to use my current lenses.
They describe my Rebel as a 'beginner' camera, though I've won competitions against 'pros' with 'pro' cameras, but the marketing does mess with my pride.
CANON EF 100MM F2.8 L MACRO IS USM LENS
I love macro photography and use the Canon basic macro lens on the Rebel. This is the stop up full-frame lens for the 6D.
It would have to be next level because this lens alone costs more than my current camera body with a tele, prime and macro lens.
SIGMA 24-70MM F2.8 DG OS HSM CANON (ART)
Another lens that by itself costs more than all the lenses I currently have. DSLR shooting out of the 'beginner' cameras is for the privileged.
CANON EF 70-200MM F2.8L IS III USM LENS
If you think the others are dear, here's your telephoto, and only up to 200mm, for less than most of my motorcycles have cost.
Rather than flash "pro" kit around, I'm looking for ways to innovate my photography. A full-frame DSLR would be nice, but for a fraction of the cash I could get myself a current micro-drone, a powerful super-zoom and the latest in 360 camera technology, which even with all my experience with, I still feel like I'm only just scratching the surface.
In a variation on photography, I've also previously explore 3d scanning with the first gen Structure Sensor. Their current PRO model is $695 (US) and comes out this summer. That'd also be on my short-list of 'imaging tools'.
If I avoided the DSLR money-pit, I'd be into five and half grand in the latest imaging tools (360 cameras, drone, big sensor all-in-one super-zoom and 3d scanner). That's 1/3 the price of a single 'pro' level telephoto lens. Wish list or not, I think I can do more interesting things with digital imaging with a more diverse set of tools.
