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Advanced Dynamic/Conditional Squid Configuration

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Hello,
We currently have a squid system which handles outgoing requests through thousands of IP addresses and hundreds of users. We want to change the system and make it more complex but we are unsure if some of our "wants" are even possible within squid-cache:

1. Replace Htpasswd users file with syncing to an external MySQL database which manages users
2. Logging which syncs to an external MySQL database
3. Conditional / Dynamic Rules, for instance:
Serving each request with a different outbound IP
If user_X serve IP_1, If user_Y serve IP_2
Pulls outgoing IPs list from a server and then rotates through etc
I believe 1 & 2 to be possible but not quite sure if you 3 is possible in squid or any other software.

If anyone would can give some guidance or is looking for a project we are looking to hire someone to help us build our this system. Email: admin@xxxxxxxxxxxxxx

Many Thanks,
Ping Technology Labs LTD
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