Planned Domain Transfer: Separate Domain, Host, and CMS - Input appreciated!

Hi, everyone! I've got a complicated client project website that we're launching this weekend, and I just wanted to consult with other Circle Members in advance to see if you spot any issues with my plan. 

Current Website: 

Built With: WordPress 
Domain: Network Solutions 
Host: Custom Cloudflare Server through a very small Third Party Company 
Email: Google Workspaces - they are a nonprofit so they get it heavily discounted directly through Google. 

I have consulted the Squarespace Network Solutions Transfer Guide and the Network Solutions Transfer Out Guide. The third party company has given me a copy of the existing DNS records. 

Here's my plan: 
1. Restore the Custom Nameservers back to their default settings (which should be away from the Third Party Company and toward Network Solutions?) 

2. Unlock the domain on Network Solutions 

3. Request the authorization code from Network Solutions

4. Complete the transfer in Squarespace per the guide 

Questions: 

Do I need to restore the custom nameservers back to Network Solutions at all or is that an unnecessary step? I'm worried that the transfer won't go through correctly if I leave them with the Third Party Company. 

The other thing I am concerned about/feel stuck on is the Email/Google Workspace. I am anticipating that there will be some downtime with the transfer, but not sure if Squarespace will play nicely with a separate Google Workspace subscription that's not run through them. Do I need to do anything special to connect it? 

In Conclusion: 

I'd like to make this transition as seamless as possible, but with so many players I am nervous. I feel like there's something I'm missing. Any observations you have would be appreciated! Thank you so much for your time. 

3 hours ago, MaryMThames said:

I'd like to make this transition as seamless as possible

If it were me, I wouldn't transfer the domain.

I'd simply edit the website DNS records on Cloudflare (as they're currently hosting the domain name records). That way you won't be affecting any of the records for other services (such as Google Workspace).

7 minutes ago, paul2009 said:

If it were me, I wouldn't transfer the domain.

I'd simply edit the website DNS records on Cloudflare (as they're currently hosting the domain name records). That way you won't be affecting any of the records for other services (such as Google Workspace).

Thank you for your input, Paul, I really appreciate it. Unfortunately I don't have access to Cloudflare- that's through the third-party provider, and it's not cost-effective to continue paying them for their services. 

This is a small nonprofit with limited tech resources, so I think keeping everything under the Squarespace umbrella will be simpler for them in the long run.

1 minute ago, MaryMThames said:

I don't have access to Cloudflare- that's through the third-party provider

That's a shame as this was the safest option. The next safest option is to remove the custom nameservers so the domain hosting reverts to Network Solutions. Of course there will be some downtime if you cannot administer the Cloudflare account to reduce the propagation delays. 

For a seamless transition, I don't recommend transferring the domain.

9 minutes ago, paul2009 said:

That's a shame as this was the safest option. The next safest option is to remove the custom nameservers so the domain hosting reverts to Network Solutions. Of course there will be some downtime if you cannot administer the Cloudflare account to reduce the propagation delays. 

For a seamless transition, I don't recommend transferring the domain.

Thank you, Paul. I really appreciate your input here, and I'll definitely keep this in mind for future projects. 

It's heartening to hear that the next safest option is to remove the custom nameservers - that was my gut feeling, but I'm new to this side of web development so wanted to check what others thought. 

Again - thank you for your time. Appreciate it!