I'm pretty sure I'm going to move from SmartOS to Helios at some point. I have to set up a VM and try out all the things I'm currently doing and make sure they still work acceptably. I may also move from Xeon to AMD EPYC, but stay on Dell hardware (because it's cheap). What I really want is to move to something like a mini-ITX Qualcomm board, but that's probably not possible yet. This is the goal because I want to compute as much as possible and I operate within my solar net-metering limits.
An autism thing I do is waffle and struggle until I figure out the "upstream criteria" of a decision. There's a shape to things that are correct. I discover the shape and use it to inform my other decisions, while still thinking critically. I know this isn't going to make sense to you, so I'll give an example.
I use the simplest tool available, originally because I was poor, but now because I'm frugal. I use SSH keys, rsync, and cron to do backups and I've been doing it this way for 23 years.