I'm a brand new ham and truly a neophyte. Wow, what a learning curve. Just passing on my experiences for correction by more experienced people and as a warning of what not to do for others.
I got my technicians license on the 14th and my amateur extra on the 24th of last month. The first week or so was playing around with Baofengs and learning that very little VHF/UHF exists in my area and very few repeaters are reachable via a HT. So then I pivoted to a DMR HT, an Anytone 878. That is a learning curve! Not only is it really complicated, but the CPS software is absolutely the worst designed software I've seen in three decades of technology. I learned just today that I could have saved 20 hours of agony had I bought the RT Systems CPS for my radio much earlier. ($25) Cut/Paste, import of repeaters, all the good stuff to build codeplugs goes much faster with that software. I also watched a lot of video from the bridgecom university series and while decent, I think youtube plus the RT systems software would have been far more productive and with less time.
For getting on the air with a hotspot, I bought an Openspot 4 which worked with merely 5 mins of setup. That was an easy step and if you're willing to pay for the easy button, press that one. If I had to do it over again with the knowledge I picked up along the way, I might have built my own pi-star for less than a hundred bucks but I was trying to learn too many things all at the same time to do it.
In hindsight, the #1 biggest regret was that I followed the dozens of hours of how-to videos for using the Anytone CPS instead of getting the RT systems CPS from the very start. If you can use CHIRP, you can use RT systems with little extra training.
The other stumbling block that I struggled with is the fact that I'm a mac user. I figured out after many hours that I needed a free copy of vmware fusion, a free copy of windows (it is legal to use without a license key in stripped-down mode), and to run the ham software all in the windows VM. That takes time, but once you get it all going then you can run all the necessary apps.
So that's what I learned on my journey so far. Enjoying the journey, but it has been a very steep learning curve!
Experts, feel free to judge my errors accordingly.