I have tried headspace before although found it's constant notifications to be quite annoying. If it makes you put in the time though then great, but the reason I mentioned 2+ years was because these things take time to become good at, app or no app (but it is worth the investment!)
Each session of the trial seemed to contain essentially the same instructions. Is there anything more to it?
2 years on subscription (though I meditate without Headspace more). There're many techniques and ideas in different Headspace courses that were quite useful for me and I added them into my meditation practice.
Except it's a lot easier said than done. I've personally enjoyed my Headspace subscription. I have no qualms with paying for it, and feel it has been more effective than all of the material I've ever read on meditation that I've looked at. But YMMV.