Could have should have … Murphy’s law right.
A leak down test would be the best way to understand the rings/lower block as
@pb4ugo mentioned or where a leak might be in the head. Compression too. Both are important. I had great compression and poor leak down = full rebuild.
There is a gap in the rings as they squeeze together as they move up the cylinder wall. No way to make it perfect no gap situation. So water, oil, air will pass -the % of loss is the issue.
I think the question comes down to what are you most comfortable with (peace of mind) and pocket book. This is your rig and you get to decide what right is for you.
For me, if I was that far in it and the head is getting TLC, I’d take the block to a shop and have it addressed to. I personally want stuff done so they are less likely to come up in the future. Iso i tend to pull the thread more than the average bear. Issues with my approach are time for shop to get to it. If it needs pistons, hard to get domed unless performance domes $$$$. Maybe light honing and new rings freshen it up enough. Who knows.
And… with a rock solid head, it will be better than it was before you started if you choose that is good enough.
I’m not helpful and only pointing out what I think are your choices. I guess’s you could assemble after head done and test, but if tests are poor, then what. If test good, worked out and saved time and $$.
Are you risk tolerant or risk adverse? (I’m risk adverse for the my rig in what life it had before I got it.)