I'm trying to move away from Posterous because of their acquisition by Twitter, uncertain future, disappearance of support and reduced performance. The handwriting is all over the wall there. I'm not looking for "free" or "cheapest" - I just want it to work well. :)
I've been trying wordpress.com lately (douglerner.wordpress.com) and posting to both Posterous (douglerner.com) and WordPress. And I have everything imported from Posterous into WordPress. I am not looking for "free" - I'm more looking for working functionality.
I had been thinking of going with wordpress.com and mapping my domain to my blog, but I ran into 3 issues which have turned into show stoppers.
(1) Several friends I've checked either don't get my wordpress.com blog notifications or they end up in their spam folder or they get the notifications sporadically. This doesn't happen with Posterous, and I can't help but think it's a problem with wordpress.com - their headers or something. Anyway, if subscribers don't reliably get my posts there's no point, so this alone is a show-stopper. In another thread somebody put the blame on Gmail, but not all my friends use Gmail, and with one person it is a sporadic problem. Plus this never happens with Posterous.
(2) The invite system at wordpress.com is a bit buggy. For example, I have someone showing still waiting to accept the invitation in one place, yet I see her as subscribed by email in another. So it's hard to tell who has accepted and subscribed and who has not.
(3) The other main problem I don't know if there is a solution for or not. Many of my subscribers are friends in their 80s and 90s. I have to make this very simple for them. I was just doing a screen sharing with one of these friends who had received some, but not all, of the wordpress.com notifications. It seems even though there is a clear "Comment" button there he replied to many of my messages by email, and so the messages went nowhere. In Apple Mail you don't see the address you are replying to - it just shows the name of my blog, so he couldn't even tell it was being sent to a "do-not-reply" address. But here, subscribers cannot reply by email, right? They must go to the web. I'm afraid I will lose peoples' responses that way.
(4) Of somewhat less importance, but would be great if it was possible, would be an easy way to add subscribers without having to make these people go through a complicated web process to get subscribed to my posts. Like I can at Posterous.
I also created my own self-hosted blog at http://douglerner.net and imported from douglerner.wordpress.com. It looks fine. But then I discovered that the post via-email doesn't take photo attachments, or set tags, etc. That part works much better here at wordpress.com. So my thought of resolving these problems with plugins on my own server won't work either.
Any thoughts on any of this would be greatly appreciated! I definitely don't mind paying extra for extra features.
The blog I need help with is douglerner.wordpress.com.