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Coding a server for a dating site? Need tips & ideas

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So I wan't to code a server for a dating site, for educational reasons. Seems like a fairly complicated task and a great opportunity to learn new stuff!
But there are some challenges that I have yet manage to figure out by brainstorming with myself. Here are some of them:

Availability: Being able to see if someone is online. Possible live updating, or is this to much? I am thinking of using websockets for this. Also, how do we scale websockets? All tutorial I see online make use of static variables, which goes against the rules of scalability.

Live update of chat messages: I guess this would be achieved by websockets? How would the server know when to send messages via websockets? I mean the insertion of the new message in the database must trigger some component of the websocket?

Premium users: Is there a cheaper alternative to paying users than Paypal?

Caching: So people will have profile pictures and more in their photo album. Obviously you can't load these from the database every time. I saw one tutorial suggesting to use nginx for caching, but that seems a bit complicated. How would you resolve something like this?

Also, how do the server keep track of users whom are online or offline? Doing a login in will of course make the user online. But logging out is a different story because people often just close their browser without signing out.
Do the server track activity and switch to offline after X minutes of inactivity?

Are frameworks like OpenFire or Firebase an overkill for this task?

I think scalability is very important.

Thanks in advance!
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