First congrats! Many of us make websites that grow all the way to 10 users ;-) But for real, really cool trust you made something that is in use. To your ques

First congrats! Many of us make websites that grow all the way to 10 users ;-) But for real, really cool trust you made something that is in use. To your questions a) what do you mean by “next level”? Is it that there are performances issues you want to fix? Features you want to add? A new design? A different/more effective way to manage the content of the site? Defining what is it that you want will make it a lot easier to find somebody to help you (i.e. do you need a web developer or a web designer?) Regarding funding, to me that seems like a question that you’d be the best suited to answer, but a few funding models come to mind, it could be based on donations, it could be based on sponsorship (a space for those proud alumni to let everybody know they made it!). With sponsorship you could have multiple levels regarding the monetary amount of the sponsorship. You could use ads revenue, but for that you’d need to be careful to not made the site a detestable place. Maybe the ads could be only by alumni instead of using something like google ads (i.e. reaching out to alumni that own business or are hiring and offering them exposure on your site) At any rate, these are just some ideas from the top of my head regarding where I’d start if I was in your situation. Good luck!