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We don't have to upgrade right now but I dont see the current work posture changing any time soon and want to keep moving the ball down the field.

see a few other people mention it and happened to me last week when upgrading a site to 1912. The configuration service / trust service don't start after upgrading the first DDC from 7.15 to 1912. The DB schema isnt upgraded at that stage as upgraded studio/start automatic upgrade not run. So a restore of snapshot of DDc before install and then retry the DDC upgrade/site upgrade fixed it for me after trying multiple other stuff it seems the upgrade corrupts those fma services somehow

Can you do some of it in a parallel fashion?

Like build out a new parallel site running a newer version of VAD?

Yes at least some parts of it or all of it.

I thought about that, wasn't sure if there was an easy way to export published app/delivery group and policy settings if doing a new site...looked into it briefly about a year ago and found some powershell-fu that looked like it could do it but not sure if there's a better way.

It's PowerShell based for export/import

I upgraded a customer of mine from 7.15 CU3 to 1912 CU1 on Monday without issue.

We recently upgraded from 7.15 cu2 directly to 1912 cu1 without any issues. I think like most stated after the upgrade you may get studio saying it needs to upgrade twice but just click through to do what it wants and worked fine for us at least. I was nervous about doing it with everyone remote too but went well

start from 7.15CU5, upgrade component by component (license, pvs, director, storefront, delivery controllers) ... make sure you've SF already in unified experience ... and before you start snapshot the VMs, it might save you

DB backup as well prior of course

Thanks everyone for the input!