I have an expert who helped me sort this out - I had the same issue as you years ago.

I setup my email folders EXACTLY the same way as my hard drive folders.  That way once I know where a document or email goes I file it easily.

Using widnows explorer (NOT Internet explorer) I keep my main folder on my desktop - for exampke: Real Estate - from there it's easy to navigate where I need to file something

Good luck

Oh, and as far as your newsletter - mine would go in my newsletter folder

Windows Explorer has always served me well

my docs

   Community info

       Oldmar

            East Lake Woodlands

Windows exploere is what I use and occasionally misfile a document!

Let it crash. Start over. Just kidding. Sincerely. Everything for me is neatly in the cloud. Not difficult, but certainly does take a few steps to place items in the correct place. Like dishes, they don't wash themselves or put themselves away. Take a bit of thought, not a lot.

Thank you for the question.

I save everything to the Cloud in folders, clearly labeled with some files being stored in 2 or more folders that may be pertinent. I can readily find anything I am looking for on any device.

For me, newsletters get stored on Mailchimp and referenced on my website.  I don't keep any secondary copies.

Items are stored by property name and offers are in a subfolder by agent name.

Misc. stuff is in the root folder.

Maybe I'm not the person to help but it would go in my newsletter pile/folder.

I file everything by the property address itself.

I have my own system which I basically taught myself. To answer your Q -- newsletter hard copy in property file (I would keep one rep sample if all digital copies are filed.) Digital copy in a subfolder for that community. Main folder 'newsletters' would be my way of doing it.

Different folders and run backup...... Never had issues.

It should be setup in the way that you think.  With your example, I would put it into the Newsletter folder.  If you have a lot of newsletters to several communities, have separate newsletter subfolders for each community.  Alternatively, have separate newsletter subfolders by month.  I would probably do it by month myself.

You also need to have standardized filenaming conventions and standardized dating conventions in the filename so that sorting can be done fast so you can find what you need fast.

I file things the same way I remember things.  My desktop consists of primary subject folders (Personal, Customers, Forms, Social and Compliance folders).  These seem to tbe the five topics I deal with on a daily basis.  In each on of these, there are additional folders based on more specifics.  This keeps my desktop fairly clean and organized.  Think of it as having a drawer at home for your underwear, socks, t-shirts, shirts, etc.  I think that it is the natural way that most people store memories and information in their noggins as well.

I do the samesame file folder structure in my Outlook email and Internet Explorer 'favorites" list.

But then again, some people need to have their desktop/noggin completely filled with stuff.  It just works for them.

I'm beyond help but am reading answers!