First time pool owner. How bad is this?

New pool owner as well, and our pool looks very much the same.

You can totally rock that plaster for another few years but we're choosing to re-do ours so we can modify the pool a bit and add some safety features

One thing I noticed is that you only have one drain - same as us. For safety, you can have that chiseled out and a channel drain installed - basically it splits the drain into two drains but you don't need to run a totally separate pipe. Quote is around $800 but it prevents some drowning risk so it's worth it for us cause of kids. Since we're draining the pool and getting a guy out here we may as well do some more work. Like how all projects start to spiral ;)

We're also adding a tanning ledge (google it) so we can lounge in the shallow end (~6k) and replacing the 500W light ($$) with an LED (~$1k for the fancy multicolor one).

Finally we're going to pebble tec the whole thing which is about $15k vs $7k for plaster.

It's definitely a good bit of coin, but we would want to do the safety drain no matter what and while the plaster we have (our is worse than yours even) could be cool for a while, aesthetically we want to have it looking good, too.

Anyway that's our experience, hope it helps. Get two quotes and know that everyone is booked for months even if you do want to move forward.

/r/pools Thread Link - i.redd.it