When is the “right time”..

So my SO & I have been trying to convince for 2 years now (on and off). When is it time to call it quits and head to the doctor? Obviously it’s been a good amount of time. We are both decently young (I’m 23 he’s 27). And let’s say I make an appointment, what do I say? 😂 what questions should I ask? And what crazy kinds of test will I have to do? 😅😅 thanks in advance!

ALSO We’ve tried pressed, OPKS, having sex every day, having sex every other, trying, not trying, prenatals and pre conception (for men), just about everything I think. My cycles about 27 days (every so often it’s thrown off by a couple days).