Totally agree with your first two points. I would also suggest experimenting with trial durations. I don't know how long it takes a typical user to setup your product and get to proof of value but perhaps it can be done in 14 days, maybe even 7.

I personally believe that, in some cases and depending on the product, placing urgency on the user can yield positive outcomes. This also grants you additional freedoms to "nudge" the user, simple example, "setup an account and earn an extra week of trial".

Good work and good luck, keep experimenting and measuring.

I'd punt on offering free trials and instead offer a 30 or even 60 day money back guarantee. This is effectively the same thing but gets you access to money today as opposed to 30 days later. Learned from this terrific video from Jason Cohen: https://vimeo.com/74338272

Yep, seeing the effect of $.50 instead of $1 for trials when there are are lot more users & trials was really enlightening. I'll most likely do that. I could even not provide bank syncing for trials, or require a credit card. Will do something like that.

Definitely going annual as well - tempted to go only annual, but we'll see.

Annual is unappealing to most subscribers - but some percentage will go for it if it's available. Like 10%ish (may vary but definitely a minority). This minority will smooth your cash flow quite a bit.

What evidence/reason do you have for the claim that annual is unappealing to most? (I'm not advocating anything here, I'm hoping to learn something.) I would assume the same thing if there is no discount (no compensation for extra risk and time cost of money), but I can only guess at how people respond to annual options with various discounts. Do you have anything more (including your own guesses)?

One data point, for TeamPassword[1] we offer monthly and annual as described and about 1/3rd choose the annual plan. Would love to learn more data points to see how our mix is versus others.

[1] https://www.teampassword.com

Putting a high sticker price in front of someone is another one of those speed bumps to conversion. As the proprietor you'd probably prefer them to go for $70/yr, but $70 is a big difference as an impulse or low-deliberation purchase from $7. I'm the annual-plan-buying type, but I'm atypical in a bunch of ways - e.g., I live in a high cost-of-living area so while I'm not actually a money-disregarding rich person, my impulse-buy range goes a lot higher. (annual = 10x monthly is very commonplace)

Has anyone ever tried:

Annual plan only available after 6 months of membership?

While I understand that sounds counterintuitive, if not odd, it:

a) offers an incentive to stay.

b) with that goal line in mind, the offer of annual when getting there has special meaning. As opposed to a random "you've stayed. You must be happy. Wanna go annual?"

Again. I hear what you're saying, but in a nudge-y / Hooked sorta way it might work.

Bloomberg (magazine not terminal) did that for me, annual plan wasn't available during sign up (though there was a cheap 3 month trial); after a few months on the full monthly plan, offered me annual plan at a discount.

I took it.