I would like to know if there are any good ways to help in remembering all the dates, passwords and login usernames.

A combination of the app Dashlane and using Google Chrome as my web browser (since it stores password information) has been a saving grace with my mom. My mom had a habit of forgetting passwords and in trying to reset them, get herself locked out of the account, and then give up and never paythe bill. Once I started managing her finances, setting up auto pay for as many bills as possible was step one for me. I don't need to remember how to get into the account in order to pay, and I know it will be paid no matter what. Best of luck!

You may need to be POA or get her to agree on a form or letter, but I had them make me alternate contact for insurance. When a premium or fee is due, or has not been paid, I am notified. This has saved us a couple of times with Long Term Care Ins.

It is unlikely forgetting a password would cause a big problem since sites usually have a password recovery option. For those of us in the real world - if the site uses challenge questions, forget proper grammar or punctuation for ease of remembering. Correct grammar does not count there. I use all lower case and no spaces. Just be consistent for all sites whatever your preference.
I use a spreadsheet for my 300+ passwords and challenge question answers. I password protect the spreadsheet (easy to do) itself and make a copy on a cheap usb thumbdrive for my file cabinet. The one password for the spreadsheet can be simpler since it is unlikely to be attacked. Even my grown children give me some of their passwords for safekeeping. I like the book idea as long as it is well hidden, but knowing me I would probably neglect to keep it current or include challenge questions.

I know it's a no-no, but I keep all my accounts, log-ins and passwords in a small accordion address book. I abbreviate my notes - Agingcare is listed as AC..
Facebook is listed as FB, etc... I used to carry my very slim accordion address/telephone book (bought in Ebay) until too many purse snatchings here. I decided it's best to keep that book home. Since I'm not carrying the address book, I put on both my iPad and Kindle note app - only logins/passwords for AC, FB, Disqus, etc... I do Not put any of my bank/credit card info there.

Website with "10 best" password managers

https://www.consumersadvocate.org/password-manager/a/best-password-manager?

My husband uses Lastpass in the cloud to store passwords. The desktop version is free. One would need to be computer savvy to use it. I am not.
He recommends another one also: 1password.

He recommends visiting "Have I been pwned?" (spelling is correct),
"Have I been pwned? " website. This will tell you how many of your accounts have been compromised and how many have been breached. @Troy Hunt.

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I use my address book for password info.

I read ur profile. You have Mom at the age of 47, is this a misprint. I ask because with the health issues she has I am assuming you are handling her finances.

First, I would check on that life insurance policy. Tell them the situation.

I wish I was there because it can be easy once you understand how everything works. Changing insurances can only happen during open enrollment that starts in Oct and ended Nov or Dec. If you want private message me.

I bought a neat little specialty notebook the other day while visiting my son; we went to a country store/breakfast place and they had little notebooks for keeping website addresses/emails/ passwords all nicely sorted. My mom did this in a little spiral notebook for years ( came in handy when she passed!). I've done this haphazardly over the past few years in a little Moleskine notebook, but I'm being more vigilant now. Write EVERYTHING in pencil so you can change it.
There is a little book called "5 at 55". It details the 5 documents you MUST have at 55, and a "digital diary" is one of them.

I keep two 3” x 5” identical notebooks with everything in them. One in my safety deposit box and the other in my briefcase or handbag. I have payments set up on bank auto pay 5 days before due dates. I have SS, pensions, investment account dividend payments all direct deposited to my checking account. I have transfers to my savings account and to a travel/vacation account each month. Easy way to be organized. Quick and easy. You never miss a payment or a check lost in the mail.

Life insurance should not lapse after one missed payment. At least in Canada, you can make up the lapsed payment. I would look into that further. Here a plan can be reinstated.

Computers can be wonderful for the younger generation for reminders. Programs such as Gmail or Outlook have comprehensive calendars that send reminders in a variety of ways, from texts, to email or on screen pop ups on phones, tablets and computers.

A good old fashioned address book is a good place to write down user names and passwords, just make sure it is kept in a safe location.

Calendars and dayplanners can be used to remind those who are not using computers about payment dates.

Many antivirus programs have a password manager. For recurring payments there is also the possibility of setting up pre-authorized payments directly from your bank account.