On the topic of selfhosting, privacy and ease of use

I've been following the talks about selfhosting, wendell have been responsible for.
I recently bought a .tech domain.
(AND NOW I'M EXCITED!!)

Now i just need to use it, live an independent-ish life on the web.

What I want from a server:
- Mail calendar and contacts. (preferably with my .tech as an address)
- Dropbox/G-Drive replacement
- G-docs replacement
- Photo/video storage and backup.
- Wordpress hosting.
- other cool stuff like a gameserver, to show off to the guys (get some geek credit, not important, but could be rad)

Now for my obstacles:

I don't know if I want to deal with the complex nature of hosting my own server for wordpress, sandstorm, yunohost, mail etc.

It seems as though that it gets complicated, and difficult and/or expensive as soon as i want to host a mailserver, make sure that my files are backed up properly, make sure that i don't get hacked all the time.

Also it looks like i can't get proper storage (by that i mean 500gb and up, for photo and video storage) without spending one million billion dollars on a deca-core super nitrogen superserver.
Right now i use flickr, pretty happy with it, but it could be cool to host it for my self.

I have signed up for a free sandstorm oasis, I'm happy with the (relatively) easy wordpress install and setup, but the inbuild document, calendar and mail apps in sandstorm seems like a b-grade (maybe even c-grade) choices in comparison to what I'm used to in google docs. (what alternatives are there?)

Right now it seems as though that I can get most of my requirements filled with:
Fastmail (Dropbox, email, calendar and contacts) 40usd/year
Flickr: 1tb storage for photos and videos (with autosync from my phone)
Sandstorm oasis for wordpress.
Gdocs????
Gameserver not really important, mostly a bonus.

Does anyone have some recommendations or experiences with hosting their own servers?

How time consuming/expensive is it?

Is it even worth it to collect everything at one place?
(I mean it's the dream right? but is it an utopic thing to aim for?)

You could make a virtualisation server and create seperate VM's for various tasks.

Buy another domain for mail and add an MX record to the DNS of your web domain so when it resolves @yourdomain.com it fetches mail from yourmail.com.

I wouldn't do any of theese before putting a proper network security system in place though. Seperate Pfsense machine + OpenVPN should be enough.

Don't start with Email, Its...difficult and you don't want to be the guy who didn't get the email from that website or a friend.

Where do you want to host this? If you want to backup your photos that will get expensive, contrary to popular beliefs storage on the cloud isn't dirt cheap. To do right anyway. Hosting at home would work as long as you have more than say 4 mbs up and a semi static IP.
If your IP keeps changing then using a server like dynDNS would help.

Digital Ocean or Linode can take something like this with ease but you'll need at lease 1gb (2 would be better). Don't start with AWS unless you want to learn how it works.

Own cloud will help with a lot of your media and backup requirements but a Google docs alternative is harder to come by.
A quick Google got me here http://onlyoffice.org/, but it looks demanding.

I would start with a YUNoHost Box (I did) and use OwnCloud and install WordPress from there.

@degan6 This is now a misconception, you can easily have an email server, just look for the all in one alternatives than going in by hand install postfix and what not. And don't be shy to read the documentation on how to use it, it really is simple.

I recommend:
For Windows: https://www.hmailserver.com/
For linux: http://www.iredmail.org/

Yo bro!
Damn, now you've got me excited again xD
Have you any experience with iredmail?
How about the combination with iredmail and yunohost? will that break anything?
iredmail's documentation states that i have to install it on a fresh debian install.. :S

A virtualization server? is that with virtualbox on my desktop?

iRedMail is recommended to be installed fresh, just to be on the safe side. Looking at yunohost website you should be able to run both without any problems, personally I would install iRedMail first then yunohost.