Updated pricing structure (pricing is hard)

Pricing is a very tricky thing to get right, and it poses lots of ethical concerns too (eg: localized pricing, A/B testing pricing, etc.).

There is also a hard-to-balance ratio between sustainability/profitability and respecting the customers (all of them). Pricing a product high might lead to higher profits and fewer customers (good for you), but this means your product is really exclusive and can only used by a few people, instead of trying to provide value to as many people as you can.

I think the best way to show the struggle of pricing is to write an approximate history of the pricing structure of userTrack.

2013-2019

• Lifetime license
• Pricing gradually increased over time from $19 to $59 to match the features set.
• The support period lasted 6 months and could be extended for 50% of the price (the default CodeCanyon terms).

Almost no-one renewed the support, as they still got updates.

2020

• Jan-March: Lifetime License - $99

This felt like a really good price point for the product, customers loved it.

• March-August: Added a new "company plan" and increased lifetime prices to $129 Personal License and $399 Company License

It soon started to become clear that it is way too hard to be sustainable having just a lifetime license, something had to change if I want to keep working on userTrack

• August: Added cheap monthly prices as an alternative to the lifetime versions, around $7.99/mo Personal and $24.99/mo Company.

50% of customers started chose the monthly version, as you could test the product for only $7.99 instead of $129
One issue with this pricing model is that the churn was really high, as the customers could just cancel their plan and keep (illegaly) using their userTrack dashboard (but without getting any future updates). I decided not to implement any DRM, as those never actually work and only affect legitimate users.

• October: Removed Lifetime License, switched to yearly plans: $59/year Personal, $199/year Company.

This pricing sounds reasonable, but clients didn't like it, sales dropped. It feels odd to pay a yearly fee for a self-hosted product

• Now (November 2020): Re-added Lifetime License, but with a twist: this only includes updates for one year, if you want to get updates after that, you can get one more year of updates for 50% of License Price.

This means that current pricing is:

• Personal: $99 License + 1 year updates. You can use userTrack forever. After the first year, support/updates cost $49/year.
• Company: $299 License + 1 year updates. You can use userTrack forever. After the first year, support/updates cost $149/year.

I am personally really happy with this new pricing structure: sustainable and reasonable for a self-hosted product (can use it forever instead of a license subscription).

The only thing left to do pricing-wise is to offer a trial version, so customers can test userTrack for 7 or 14 days without paying anything.
I think this is really important for a self-hosted product, as the main push-back is the idea that self-hosting takes too long to get started with. If clients can try setting up userTrack without paying anything, then they will be a lot more likely to consider purchasing it.

You can view the pricing table here: https://www.usertrack.net/pricing

What do you think of this pricing structure (one-time license + paid updates) for self-hosted products?
As a customer, would you prefer a different pricing structure for such a product?