I had an orchid that sat in its pot for three years before I realized the whole root system had basically seized up. The roots were packed so tight the medium had broken down into mush and water just ran straight through. That's the worst-case scenario, but yeah, two years is genuinely around the time to think about repotting.
The main signs are what you're already seeing - roots circling the pot, poking out drainage holes, or visible above the soil surface. But also check the potting medium itself. Orchid bark breaks down over time and compacts, which kills drainage and root health. If water goes right through without the roots absorbing anything, or if it pools and sits, that's a red flag. Another thing: if your orchid's growth has totally stalled despite good light and feeding, the medium is probably shot. Phalaenopsis especially need that chunky, airy medium to thrive - regular potting soil will rot them out fast.
The best time to repot is right after blooming ends, when new growth is just starting. Use orchid-specific bark mix, not regular soil. Go up maybe one pot size if the roots are truly cramped, but don't go huge - orchids like snug containers. Water well after repotting and then back off for a week or two to let any root damage heal. In your case with the crowded roots and two years elapsed, repotting will probably help it bounce back.