> I'm always a bit wary of approaching these ideas though because I feel like nobody would ever pay for small web stuff?

There are 2 billion internet users.

If you can sell a $5 subscription to just 40 000 of them (0.002%) [1], you can retire. There will always be someone who will be willing to pay for something. The problem is finding these 40000 people.

[1] 40000*5 - 30% various commissions - 50% tax = 14000 dollars a month, 168000 dollars a year unless I'm really bad at math :D