After researching a bunch online, to backup our MacBook Pro I decided to go with Backblaze. While I researched other services, Backblaze came with great recommendations from coworkers and touted ease-of-use as one of their main features.
Setup was dead simple and for only $5 / month I could have unlimited data backup offsite. The entire upload process took about 6 days (have approximately 1TB of data on my Mac). After that Backblaze has continuous incremental backups that happen in the background.
Note: Coworkers of mine have mentioned that they have a 3rd backup solution (external USB hard disk that syncs via Time Machine and is taken offsite). I think this may be overkill but will consider in the future.
iCloud Photo Library
Implementing a cloud-based backup scenario in addition to our onsite backups solved the majority of my data backup concerns. However, most of my personal computing is done from my iPhone (heck, it's how I published this blog post!).
Generally I don't have any persistent data on my phone - most of my content is stored elsewhere (mainly in Gmail, Drive, etc.). The one glaring exception to this was my photos. I normally backup my iPhone via USB every month or so, however if my phone were to vanish I'd be missing out on my most recent photos.
Additionally I have thousands of pictures from my teenaged years stored on my Mac in Photos. These are synced to my phone but I've always treated them as a separate "library" compared to my iPhone photo stream.
I had been hesitant to try iCloud Photo Library in the past for a few reasons:
Library size - I have upwards of 30 GB of photos that I would need to store, which would blow past Apple's free 5GB storage tier.
The transition process - I've read horror stories of people moving their photos to iCloud and having duplicates, missing photos, etc. I had a similar experience when moving to Apple Music a year ago which cost me a full day's worth of data cleanup.
Given my recent success with Backblaze, I had confidence in giving iCloud Photo Library a shot. I had also noticed that Apple dropped the price of the 50 GB iCloud plan to about $1.29 / month which was well within my budget.
I started by enabling the service on my iPhone first. I did this to see if I could use a hybrid approach as a potential solution in the future: my phone photos are synced via cloud and my older photos are synced traditionally via Photos app. Unfortunately this isn't an option - you lose all manually synced albums when enabling on your phone.
The upload of my iOS photos only took a few hours and I had plenty of space left in iCloud so it was time to take the jump and enable on my Mac. Essentially for the first time this was when my two libraries would be merged - in the cloud no less! I made sure to have backups of my data should any issues arise.