This isn't a competition.
If you want to say "hi," then say hi. If you want to say, "Let me take you away from that loser," then don't.
I'm glad you are on your feet financially and things seem to be looking up for you. That is wonderful news! So reach out platonically if you would like to. Will she make a comparison, and decide you're the better deal? Possibly. Or not. But don't go into the communication with any of those expectations. You're just being friendly. Period, and I mean it.
And cultivate other friends! Including female friends, I might add. I suspect this is more a yearning for nostalgia than anything else. And maybe you feel you have fewer alternative prospects. So get out there and make friends and you might have some alternative prospects.