I have had my company purchase company plans for products I use as free or free for personal use.

I will never recommend Google Apps for Domains or whatever it is called now after they dicked around.

Probably not from my personal use, no.

But for company use, I'd rather pay for something I'm happy with using personally or have had good experiences with in the past, rather than rolling the dice on something unknown.

Then why offer it to begin with? Presumably a company does so because there's some form of value for them.

Most of my recommendations for services to use come from my friends who have either used that service on a free plan, or a paid plan. It matters very little in terms of the network effects of their service whether or not you're on a "free plan". See GitHub's free subscriptions of CoPilot for open source contributors.

You might be happy, but then hit a free limit and decide to pay to be even more happy The chance is low, but not that close to 0%

There could still be word of mouth that leads to paying customers. Or circumstances change and the paid plans are worth it for previously free customers.