Lol... I'm glad I walked away
Follow-up for you diagnostic guys:
I've been spending more time in and intend on moving soon to a much colder climate. I had to resign myself to the fact that this isn't something that can be band-aided with a different starter.
Here's the numbers, first is hot compression, second is hot compression with oil, and last is a note about which valve is leaking, working from pulley to flywheel:
360, 390, E
250, 300, I
350, 350, E
350, 360, E
I replaced the head in April of last year due to cracking the OG head. I now have 22,000 miles/11 months on what was a brand new out of the box Topline head. At the same time that I replaced the head, the starter crapped out (on the first crank as I was purging lines) and the GP relay stuck on... bad luck, Murphy's law, whatever... After getting everything sorted the Caddy went from starting immediately in all conditions to requiring excessive cranking, even when warm, in mild air temperatures. There was no lead-up to the hard starting, it came suddenly with the head job.
In talking to the company that sold the head (Aluminum Head Rebuilders in OR), they mention that the head has a one-year warranty but with the many hundreds of Topline heads they've sold, there have been no complaints.
I now have the valve cover off and when pressurizing #1, it's leaking rapidly into the exhaust while the lifters are free spinning so it's not a lifter problem, at least on this cylinder.
Chris