I've actually been putting numbers on this: there are many fans of NewsBlur, apparently, as a replacement for Google Reader, so that's $12 a year; I'm worried about being tied to my Gmail address, so I finally got around to setting up a vanity domain address which forwards to Gmail and that's going to be about $10 a year. So I'm up to $22 a year, and I haven't looked into any free or paid replacements for Google Calendar or Analytics...
Between Google retiring stuff and Twitter's ongoing war against client developers, I'm seriously considering just packing up and self-hosting everything I care about on my VPS.
I've been thinking along the same lines. To begin I'd like to just mirror everything on a VPS (email, rss, calendars, dropbox, music library, youtube playlists, bookmarks (for me: pinboard)) on the VPS.
Then I'd have cobble together whatever oss webapps I need to access all that remotely, and then lock the whole thing down -- ideally only allow external access via ssh and then set up my phone/laptop to VPN through it when I want access.
It would be at least a day of work to set it all up but I think I've almost reached the requisite pain point.
EDIT: and it would be nice if I could run phone numbers through it as well via something like http://voip.ms/ ... if anyone is aware of someone doing something like this and writing it up I'd be interested to know, I haven't come across any setup like this.
pobox.com (http://pobox.com/pricing) is a fairly stable domain for email with lifetime hosting for as low as $20/yr (forwarding only) or $50/yr (hosting)
I think NearlyFreeSpeech.net is probably about as stable a forwarding host, and cheaper. (I host my http://www.gwern.net on Amazon S3/Cloudflare at ~$4/month or $48, so pobox.com wouldn't be cheaper in toto unless you meant web hosting rather than email.)
