Should I switch to Apple?

I have been a long time Windows user, but here recently I have been thinking. Should I switch the whole family to Apple? Here is my current setup.

I have a Home server that serves as a media hub and the whole family’s storage and backup. Each member has their own drive on the server that is shared with them for their backup and storage. One drive has about 2.5tb of movies (which I have ripped from our DVDs and Blurays) and music and another drive has about 1tb of family pics and vids Total of 5 drives. They are all backed up to a 4 bay external system so everything ends up in that one place. Each family member (5 total) has their personal laptop that they use that is connected to the server. As of now we use the Plex apps to access our media. Now with Windows 8 on each they have their Netflix, Hulu and a few other apps they enjoy. We are not really dependent on MS Office but we do use it a little. Wife uses Photoshop CS6 every day. Kids game a little, biggest game being diablo.

I use Roku on each TV (3 total) with Plex to be able to have our movies on the big screen. I would use Xbox but I don’t want to have to pay for something twice just to be able to watch Netflix.

The kids each have Kindle Fires which also connects to the home server. Now my problems. It seems like every other day (maybe exaggerating a little) I have to re-share one of those server drives, or fix some kind of connection or backup issue, pretty much all the "Windows" nuisances. I don’t know what it is but to me it seems like Windows 8 is not as stable as 7 was (constantly having to do something). I used to "enjoy" all these problems, but as the kids get older there is just no time anymore. The perfect solution would be to just set it and not have to worry about it anymore.

A few questions are. Could Apple do this and DO IT BETTER? Would Apple be able to handle my home network would Apple TV be able to replace my Rokus and with it could I watch my movies from my server without needing Plex? Would an Apple setup be just as aggravating as the Windows setup can be? The big question is would it be worth dropping about 7 grand on this? I know nothing about Apple other than having the 1st gen ipod touch but that’s been long gone. I am familiar with Windows and know it really well. The kids really like having "apps" now in Windows 8 they are easier for them. MS has a small apps store compared to Apple but it will grow eventually (at least that’s what I keep telling the kids).

So if I were to do this it would be getting: a Mac Mini (Server), 5 Macbooks, 3 Apple TVs, and maybe a couple of ipods and an ipad.

Let me know your thoughts. Like I said I know nothing about Apple or OSX other than what I played around with at the local store.

I have posted this in both Apple and Microsoft forum to get both sides. Not looking for any trolling here just some good advice.