Is my contractor setting up my proxy solution correctly?

TL;DR: we have three "fake" employees and our proxy system can't afford to have holes in it.

I hired a contractor off Upwork to set up proxies so that our offshore VA would be able to log in to our three "fake" employees [that I created on prepaid phones--G Suite email address, LinkedIn, and Facebook accounts].

He ended up setting up something with Pritunl and DigitalOcean droplets. So instead of just a Proxy solution we're using servers in San Francisco, one droplet per each of our three accounts. From my understanding it's a full-blown VPN.

Today's the first day of operation, works fine. I've just been using Chrome on incognito mode to log in.

HOWEVER, I am worried that we're not covering our trail thoroughly enough. Won't the other internet traffic, from my email app (plus whatever digital signature my Macbook has) be a red flag if it shows up on all three droplets (or servers or whatever)?

Also, I keep the phones with me, while the DigitalOcean servers are in California. Will the location difference be a red flag as well?

Or is our solution sufficient as is?

Appreciate any feedback, and thanks for giving a n00b a hand--

Sick

A proxy by itself will 100% expose their real IPs. The solution you're using it not secure.

You need to either move to a real privacy browser like MultiLogin or ask your contractor to convert the proxies to VPNs, otherwise any website you connect to can see your real IP as clear as day.