Seems on par with what ngrok charges? Of course I could set it all up myself but the $60/year or whatever is cheap enough for me to let someone else handle it.

Why bother with the .99? Why not just charge €6 / €5 - the .99 gambit is, IMHO trivially deceptive and - speaking for myself - if I am presented two purchase / subscription choices that are approximately equal, I will usually choose the product that acknowledges the fact that I am capable of rounding in my head.

How can the free trials be different lengths depending on what paid package you choose?

Good question. This obviously isn't well thought out. Why not just do the annual trial for 7 days? Would they seriously not let you sign up for monthly plan after because of that?

Thanks for your feedback... why not indeed? I've updated it within product page (and In-App Purchases). It'll probably take a little bit for the description in the App Store to update, though.