I've not worn socks or trousers since the end of April. My dress shirt is all the students see. Sandals and shorts cover the rest.
If you're drinking and teaching, you wouldn't last long online, to be honest. Teaching for 8 twenty five minute classes with a 5 minute break in between them in a row takes more than a fair bit of concentration and energy, at least for me.
I've got a buddy who turns 50 next year. His plan is to get a retirement visa and teach online, rather than continue to do classroom teaching as he won't need a non-b/wp anymore.
If I had paid more attention to him last year when he started teaching online I'd have probably quit my reqular job if I didn't need a visa for the wife.
$2000 USD/month is easily achievable while working at home.