What to keep and what to toss? My cluttered Cloud

I tend to like to hold on to things. My father used be the tosser/organizer in our household. He would sometimes get carried away and toss important stuff. I on the other hand would keep too much stuff and the important stuff would get lost in it all. I am trying to find a happy medium between these two extreme styles. I've quickly filled up my free cloud storage at Google Drive and Drop Box (I am now going to open a Skydrive account at Microsoft for additional storage). I don't want to pay for cloud storage I would rather put that money towards other things. Over the years even a small cost adds up.

I've been catching up on my backups to the cloud. Doing this I've noticed how bad my computer filing has been and how inconsistent I have been when it comes to putting things in the right folder. So I am cleaning up  sweeping out and reorganizing as I go along. What I am discovering as I go along is:

1. I should try to limit the number of folders I have because that it over complicating my filing.
2. I should toss duplicates because I am backing up to several places anyway.
3. I need to keep the collateral information separate I have some merged with my own line.
4. When it comes to backing up first save what can't easily be replaced ie stuff that's not already stored in digital form on a reliable site like Ancestry.com or Family Search where I can access again.
5. All my important documents linking generations need backing up no matter how easy I can replace them.
6. Name my files appropriately so they will come up in my searches. I sometimes download and don't name something or give the file an obscure and can't find it again.
7. I should backup any new document or photo I get immediately, otherwise, I will forget later whether it had been backed up or not. I don't have enough space to back up everything over and over.

The advice given on "The Hoarders" show regarding keeping and tossing can also apply to my digital files. Can this info be easily accessed again? Is it irreplaceable? Do I really need to keep everything I've collected over the years? I am finding that some things can certainly go without compromising my research. The Free storage offered by most cloud services is actually more than enough to keep my important stuff. It's just going to take me some time sorting out the important stuff. I feel like one of the Hoarders not wanting to part with anything and wrestling with every file I have. I am starting to let go slowly.

Thinning the volume out is going to help me focus and find what is most important. I won't get a headache every time I open my genealogy folder.