Release often vs. sell upgrades

I usually only announce things on the blog after I’ve decided what to do and how to do it, this post is different, in this post I’m sharing a business problem that I really don’t know how to solve (but don’t worry, I will solve it somehow), if you want more posts like this one please respond – leave a comment, send me an e-mail or use the contact form – just respond somehow.

I’ve announced that in 2012 I’m going to try and release a new version of yaTimer every single month – this means that every month I just put a version number on the current development version and release it to customers.

This means to changes between any two consecutive versions will be very small – those add up, the first version of the year will be completely different than the last version of the year – but version to version the changes are likely to be minor.

I’ve also announced that some time in 2012 I’ll start charging for updates, after the one year of free updates you get with a new license, obviously (I’ve always meant to charge for updates but I just haven't set up all the required infrastructure yet).

But now we have a conflict, since the changes between any two versions are tiny there’s no incentive to upgrade – when you free year of upgrades is over you will be asked to pay for the next update – but that specific update will contain just a few bug fixes and one or two small features, not something that looks like it’s worth the money.

So what are my options?

• Return to the two versions a year release cycle.
• Release often but don’t include any major new functionality except in major versions (or in other words, release bug fixes often but new features just once or twice a year).
• Sell only subscriptions – so you don’t pay for a specific update.
• Design the update process to highlight the fact you are paying for an entire year of updates while hiding the fact that what you are getting right now is two bug fixes and one minor feature.

I don’t like any of those options, what do you think?