Thank you everyone for the great tips. Been using an eSim for quite some time with "hit or miss". Last was a big miss because I didn't follow some of the settings. Had great success in US and zero Rogers roaming.
I've bought all my eSims here (they also sell virtual Sims if you need a local number):
https://www.getnomad.app/en
The installation is pretty simple. Either print off the GR code or send to someone to scan off their phone.
No need to use this but here's a referral code: JENN68SC that gives you $3 off (full disclosure I also get $3 in the process)-- their data super inexpensive $9USD for 3 GB over 30 days for example.
Happy, safe travels everyone! May your 2024 be full of sunsets on the waters, laughter on the high seas and storms only when you are tucked in safe!