People, no. Companies, yes.
If a web tool saves me and my team at work a bit of time for $5/month, yes, 100%, swipe the company card! Sure let’s buy another JS table library.
But if I’m working on a personal project, or I have to pay for said tool with my personal card, probably not. I’ll spend the time building my own solution from scratch while never actually finishing my project.
On the other hand if you are targeting companies, just charging $5/month is leaving money on the table. If a company is willing to pay $5/month they are almost certainly also willing to pay $50/month.
It's as complex for me to spend $5 as it is $500, and businesses would approve it equally... but if I perceive it to be excessively priced I won't even try to.
I found that selling to some companies comes with a lot of bureaucracy attached.
The last company we signed up to our service took 3 months and at least 4 hours of paperwork, I personally wanted to just tell them to go somewhere else but we kept getting emails from the dev team saying sorry
Also depends on whether company is building it for themselves or a client.
Just the licensing/subscription mess can be detraction if now your company have to tell your client that they need to pay for some 3rd party thing, even if your client have no problems with it it can take months if bureaucracy machine is slow
A former colleague makes it an interview question. He asks the recruiter what the procedure is if he wants to buy a product or use a service under $100/year. If the bureaucracy is overwhelming, it's a major red flag.
When I was working at Cisco, the general rule was to get manager approval and just go for it. Of course, these days, there are security concerns but for most cases, it's not a problem.
In a different company, it was sooo hard to get anything that they refused to buy JetBrains IntelliJ and forced us to use Eclipse. Most of us ended up buying it ourselves.
I would definitely pay a small amount for a tool. What I would not do for a personal project is pay $150 every year to renew a small wordpress plugin.