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The usual use case for paying for something you could self-host, is that you don't have to self-host and therefore manage it. Someone else deals with installation, updates, and ongoing availability.

For something like this there is perhaps extra factors like someone else worrying about abuse by malicious users and the resulting risk of being black-listed by spam filters.

At my work, getting approval to pay for this would take about 5 minutes. On the other hand, if I had to provision a server to self-host, I might be lucky to have this done in the next six weeks, depending on how IT is feeling when I ask.

Here we'd also have to go though a vendor review (security, legal, etc.)

I can easily envision a non-technical person spending a few bucks for this because they don't know how to set things up without help. I don't see that working at $99/month though. It's WAY more than most bit.ly plans for a vastly more limited product.

That's a great point, thanks for mentioning that! I'm gonna do some pricing research over the next couple of months to see what the optimal pricing is for a tool like this! :)