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Milking money out of me on a regular basis, adding to a line-item in my budget, feels predatory - as a developer, this turns me off because it doesn't actually benefit me in any way - I'm paying for your inability to fund yourself through multiple iterations of software development cycles. Put a fixed price on the product, charge for upgrades when - and most importantly: if - they happen, and it would be a done deal in my case. But right now, I don't want to have to deal with your regular charge against my credit card. Too much hassle, and you haven't been in business/released enough software, long enough for me to believe its going to be worth a year of charges.
What I'm trying to say is that your "return" from this product is obviously contingent on how much you use it/what you make with it. If you have 95% confidence that you'll produce enough to net a positive ROI over and above the fixed price, then yeah it's more convenient to buy it once. But especially for a new product like this, I much prefer a subscription model because I have more control over my costs and I can't yet anticipate my true benefit. It's a win-win: software maker gets to push frequent updates and ensure a constantly improving experience, and user gets to check-in frequently and re-consider if they're not getting enough value.
If you buy this software for 299.00, you can use it for a month and then decide its not for you - you've lost 299, but you've still got the software on your system, and can change your mind 3 months later, if you need to, and still have a valid, working tool.
I dunno, I just don't like the idea of having to be beholden to a company, every month, for the right to use a developer tool that I'd be happier having a permanent installation of .. it reeks of the trappings of a walled garden, and even if the bells and whistles are worth the hassle, the politics of the situation just rubs me up the wrong way.
I'd be much happier buying a tool I'm going to use, at my own discretion either regularly, irregularly, or not at all (my choice), than have to ask permission to use it every month. Its the asking-of-permission, expressed as a subscription model, which is the core of my disinterest.
(I've signed up for a 14-day trial, anyway, because the tool interests me enough to warrant further investigation, but unless I find some serious bells and whistles, I'm quite sure I'll be throwing it away after the trial..)
I can understand your unease given how subscriptions have been abused by unscrupulous parties in the past, but there's much less friction in cancellation these days. Ultimately I'm just finding it hard to understand why you'd deliberately create a fixed cost for yourself. I'd rather have the ability to consume a product when I need, and pay for that and no more.
I haven't tried PencilCase yet, but it looks like a great product with solid implementation. Good luck to you guys.