Many long air roots; repotting?

[colormydreams]

Hi guys, newbie here. My boyfriend got me this orchid about 2.5 years ago and it blooms regularly (it has buds on it right now, actually, and the last batch of flowers finally dropped off maybe 2 months ago). I've replanted it once with an orchid bark potting mix. That was about a year ago. It had a lot of air roots at that point, but also plenty in the ground.
My problem now is that there are very few roots in the ground but the air roots have multiplied and are very long (see pictures). It still seems to be healthy enough, but I'm afraid it's going to fall out of the pot (all the roots in the ground on the one side have rotted away and it's pulling out of the bark mix). Should I repot it? Is it in too big of a pot? Too small? I'm afraid of breaking off any of its long roots.
Any advice would be great! Thank you!