> I'd love to make that I think would honestly be worth a small subscription ($5/mo maybe)

I buy a few things for web dev side. I'm a sample of one but I avoid /mth pricing for most stuff if I can and prefer annual. Maybe me but the 'another monthly subscription' feels annoying as much as I respect I want this for my own business.

Will almost always start using free first then pay if its business beneficial to feature enrich of scale.

I think your best focusing on free and getting users. Once you hit a threshold you can ask for some $$ and some people will feel that's reasonable. If you start paid I suspect you'll have little chance of growth unless you come out with something truly amazing.