I don't think most of those that you list are really substantive moves.
Certainly moving from dropbox to spideroak or ... someone like spideroak ... would give you the ability to encrypt independent of the provider, perhaps with duplicity[1] or this other method I like[2].
But moving from gmail to fastmail doesn't seem like ti buys you much.
I think the two biggest, substantial moves you can make are providing your own email and providing your own dialtone. I do the former, and have for almost 20 years ... but I haven't gotten my act together yet to do the latter.
What you gain, provided you own the equipment and rent the rackspace, is you are the recipient of lawful orders and legal actions. you are contacted and you are required to respond. Not your ISP, not your provider, not some third party ...
That's a big, substantial difference. Sure, you still need to worry about your traffic out in the wild, but as far as the host itself, you have complete control.
Cost is a difficulty, but consider a 3-4 year old 1U server from ebay ... more than ample to handle this very light workload ... and then maybe $50/mo for 1U of rack and power, given that you won't use much bandwidth at all. Then there's some kind of VOIP peering/connection/whateveridontevengetit that you can get for $x per month. Basically, instead of getting a POTS line in your rack, you get some kind of voip peer from a bigger voip provider. Or something.
But consider what you're buying here: You are a peer on the network. You're not a consumer - you are actually taking part in the Internet. Legally you are a peer as well, as you are a property owner, not a rentier, and you are secure in certain physical rights to your rented space.
That's a substantial step.
[1] http://duplicity.nongnu.org/
[2] https://news.ycombinator.com/item?id=6554313