itsjoshbruce, 
I have an affinity for: Wait until the last responsible moment.
I've been contemplating Continuous Deployment on my personal site for years: https://joshbruce.com
But, before I did, I embraced the @jezhumble line: If it hurts, do it more often, and bring the pain forward.
I could deploy my sites in less than a minute using my phone by the time I hit the ceiling of the manual process I used.
Becca and I are ramping up on TIA: https://the-irreverent-agilists.com