ArcGIS Pro: Most Cumbersome
As a user of Esri products since 1987 (started on ArcInfo 3.x) I find ArcGIS Pro to be a great improvement over past software products. There is definitely a learning curve and a need to change workflows, but I think Pro is the future (Esri says it is so you might as well accept the inevitable 
). As others have mentioned, ArcInfo users had similar issues when moving to ArcInfo 8. It too lacked basic functionality (didn't even have an measure area tool!), but my staff of 15 and I quickly moved over. We also expanded the utilization of the product to over 300 staff members. I think the key to working with Esri products is understanding that you are supposed to work within a suite of web-, server- and desktop-based tools. Figuring out how to make them work together is the key to success. It is not trivial but will pay off!
A couple of other thoughts:
- As a GIS Manager, and later as a CIO, I led multiple technology transitions the included introduction of email (I am old), more ArcGIS migrations than I care to think about, migration to cloud-based applications (Office 365, enterprise content management system, human capacity management system, implementation of mobile devices, contract management system, ...). In almost every case the transition to something new was met with resistance from users and technology staff. The key to success was always to have a plan, stick with the plan, work closely with the vendor and engage the customer at all levels. Remember to be ready to eat crow when things go south temporarily. Smile and be positive, it pays off!
- I have found that when working with software vendors the most product approach is not to wail and call their product a piece of c##p. Instead, carefully document issues you find (make sure they are reproducible), engage with technical support and your customer representative in a professional and courteous manner. Call them out when things are not working (be ready to prove it), congratulate them on things that work well. I can think of only one case when this approach didn't work, and that was a very unusual situation involving a buyout of a company and an attempt to eliminate the software product we used in a very short period of time.
Less I be accused of being a hopeless Esri-lover just ask around (ask soon before they forget me since I recently retired). I was hard on them, but fair. They were the same back to me and it was an excellent partnership!
Hope this helps!
Just adding some thoughts from a recent training session with more depth.
Some of the ribbon designs choice are... seriously impractical. Having half a dozen 'save' buttons littered throughout the ribbon which then block further edit or save operations is just silly. I collected them all and put them on the quick access. Whichever one isn't shaded out is the one that needs pressing, just save it and let me get on with my work, darn it!
A better design would be either to have one save button function that saves all changes, or when you leave a section that has unsaved changes to popup a "Do you want to save your changes?" dialog instead of letting users wander off and have to somehow find their way back to the section that needed saving. Whichever one that was...
Same for File - Print, oh no, I mean Share - Print. I realise again that it's an intentional design, but changing a globally-understood workflow that has been in place for longer than the designers have (probably) been alive seems a bit short-sighted. Much like Chromium removing backspace navigation because some inept users were wiping out their forms. "If it ain't broke..."
To the quick access with you too, print button. To rub salt into the wound, 'print' isn't even a searchable term in the command filter to even find the print button. I know that the digital age has rendered etching images on flattened tree carcasses almost archaic, but it does needs to be done every now and again.
The only risk here with adding more and more to the quick access is that I will eventually end up with every tool I use in the in the quick access bar, in which case I guess I could just turn off the ribbon altogether and have something that looks a bit like ArcMap, but more disorganised.
That's nice, great work.
I'm not really that cheesed off, just venting at the design choices. In truth we had a dev meeting recently where we looked again at migration from Desktop to Pro. There are some good reasons to do so, especially if you're an Enterprise shop (which we are), and if you're doing 3D well Pro just blows ArcScene out of the water.
We're thinking of pushing forwards our 2025 acceptance milstone. Maybe 2023.
I've actually struggled with Desktop for years because I used it so little, yet I have to support students who use it. I dug into Pro just the other day and am already making maps, editing tables, running tools on my data, today I am looking at creating 3d buildings from footprints in some 2d data, wish me luck.
