I was going to suggest TripIt, but it looks that didn't work for you.
I keep three sets of records. One on Word, one in iCloud and Apple calendar and one on Excel
The first is a paper record in a binder.
I create a Word document, a page for each day and write the necessary information on it.
Most info is in black Ink, but reservations and tickets that need to be purchased are listed in all caps and IN RED with a due date.
Hotels or day tours that are paid for, or booked, I increase the font by one and I bold it.
After each printed page, I print out the receipt, booking information or email or copy of the ticket or confirmation and put right behind the day page.
I also add the URL for the hotel or event. In Word, the URL automatically is shown in BLUE.
Instructions on how to get to a location are in GREEN
If driving, I list miles/Km from point A to point B and travel time.
If I am taking public transportation, I list beginning station, number of stops and exit station. All this information comes from Google Maps.
So for example, "from hotel, walk to Tottenham Court tube station, take Northern Line towards Battersea, change at Embankment, Take district line towards Wimbledon, get off at Sloane Square and walk 10 minutes, 0.4 miles to Flower show entrance. Follow the crowd. etc.
Not only do I print this out to place in a thin binder that stays with me in my carryon daypack.
I also save a PDF of the entire itinerary and save it to my iCloud. On your iPad or iPhone, you can access the this PDF file from your Files App or download it to your Files App.
I also send a copy to my wife's email, so we have a third backup. (she doesn't know how to use iCloud, but saves everything in her Mail app.)
NEXT, (and this is where Apple shines (IMHO)
I save every email confirmation as a PDF file, and I upload to my iCloud in a Travel file.
Then on Apple Calendar, I list every event, including flights, pre-booked shuttle pickups, hotel (as a check in time or as a day event.
To enter a time, you must choose "Floating" as the time zone.
In Calendar, each event , right click-->Info--> and Add Notes, URL or attachments
I attach each PDF file that is in Travel file in iCloud to the event date.
I also enter the address (location) on each event entry. Many times if you start typing in the name of the hotel in that line, Apple Maps will insert the correct address in the apple calendar and you click OK.
That way, at a taxi stand, for example, I can look at my Apple calendar, click on the hotel check in time and the address will be there to tell the taxi driver.
Or if I am driving, I can click on the address listed in Apple calendar, and Apple Maps will ask if I want directions and begin a route to my location.
Once at the hotel, if there is an issue at check in, I can click on the attachment I saved on the event date and the PDF of my booking or receipt will come up as a PDF. I can also bring up tickets that are attached in PDF form or I have stored in my Apple Wallet as a pass.
By having all this information available on my Apple Calendar app, I rarely have to pull out my binder. But god forbid, I lose my iPhone, I have a paper backup of everything. And My wife has a copy also.
Finally, I keep an Excel file,
that lists by date, the costs of every events, the hotels, the meals, transportation costs, etc.
If I am going abroad, I use two columns, one in Euros (typically the price I was charged on my CC) and the second in USD. (that I use Apple Calculator to easily convert from Foreign Currency to USD or later that my CC company has already converted to USD at their good rate.
Is this a lot of work? YES
But for me, half the fun of traveling is the planning.
Now all of this assumes you know how to use all of the Apple Products. But as you state, you are fearful of tech, then
this is all going to be too much for you.