In my world, it has to be handy or it will not be used.
I use a Wiki which is the simplest database that is: fully searchable, relational, extremely flexible, fast, and cross-platform. It will sit in a cloud if you wish. It can evolve with you. It is the epitome of elegance. What else can you say about twelve lines of code?
Can you say,"Wikipedia"?
My whole file structure involves "of"ness and "about"ness.
Of refers to the subject content category directly. Family might be such a folder.
About refers to all the things that could involve that subject. Tags are another name for aboutness.
A Folder OF Family might be ABOUT documentation, wills, apology letter to mom, diploma, etc. would be some tags for family, say.
That may be too convoluted for you. Let's move on to the tool I want you to try.
While I'm thinking of it, you can decide to use your wiki in the cloud or on your own drives.
Your Security has been baked-in. For the following demo, the user-name and password is provided at the site. admin, 12345 (naturally you would use real ones.)
Try a password protected one at tiki wiki See how easy it is to use. Have a look at the features. Now, the bad news—it's only about 12 lines of open-source code. I keep a copy of this on my hard drive (to keep my MacOS 10.13 "documents") handy.
If you don't like that one, look at PBWorks.com which is where I keep my "public" personal files, my class work (handouts, assignments, projects, etc.) my reference articles, a working-copy of a dictionary of pre-press terms (published on Prepressure.com in final form collaboratively with others. etc.) etc.
Anything you're unfamiliar with is "strange." Do yourself a favour and move beyond your comfort zone.
All you have to do to "TAG" your page/file etc. is to add a line of information anywhere in the file such as: TAGS: Resume, CV, Curriculum Vitae, My Story, Me, I, Myself, First Draft, etc.
Then, to find that page (and anything else that shares the tags) enter the tag is the search field, press return. Boom!
Is that too tough?
EDIT: Call me hard-headed; but, I must get you to at least visit a site to allow them to tell you about their features directly. I'm convinced that you will be impressed to the point of trying out their solution for you.