Will this work?

I'm looking to send at least 2,000 emails per day from Gmail. As you know, you can only send 500 emails/day from 1 regular Gmail account, so I'll have multiple accounts running.

I've heard talk about those chrome extensions where you can input your proxies and essentially have multiple windows open, with each window on a different proxy configured. Is this enough to cover my ass or should I look into a multi login tool?

Bump

No need to use multi login tool...
easily create or buy some gmails will be fine,
It does not matter to use 1 IP to handle 10 Gmails...

the ips will still get banned over time though