Advice on OS update process from OS 10.14.6

[MarE66]

Hi All, Who's willing to bring me back to the Future?! 😛 I am a relative newbie on this forum and apologize if this post is a bit convoluted..bare with me.
I have an iMac 2019,1, 5K 27" with original hardware; 500G flash drive, 8 GB ram; purchased new in 2020. Running OS 10.14.6
I won't bore you with the OS "why" details. I am now ready to upgrade my OS. I am also planing to buy a new iMac 2024. I would like to keep my 27" primarily - bcz I use it as my "TV" for streaming - for at least a year or two. I Love this model and have never had any issues with it. So I'm a bit nervous about bringing this device out of the OS dark age. I have resolved/removed the old 32 bit intel issues.
Questions:
1. I am unclear based on my imac config. what the best / safest os upgrade process is: incrementally from 11 on.. or can I jump to the most recent-appropriate OS for my imac?
2. Which recent OS can my iMac reliably & reasonably handel? & is it worth/necessary for me to add 8 GB ram (for 16GB total) to handle 'modern' (lol) OS. I am thinking on resting this baby on Sonoma but not sure.
3. Back ups: I have used TimeMachine via external HD - G drive 1 TB w/USBC connetion for all my backups.

I will ask follow up post regarding advice on which new imac 2024 I should buy based on my usage. However, I am wondering about the optimal migration process as I am aware there are several options. My thought is to set up my new Imac clean and then migrate old data but not clear on how to do that.
This is the first time in 30 yrs I've been this far behind with OS updates.

Appreciate any advice you all have to offer.

 

[Bigwaff]

1. I am unclear based on my imac config. what the best / safest os upgrade process is: incrementally from 11 on.. or can I jump to the most recent-appropriate OS for my imac?

Latest macOS version your model can run is macOS 15 Sequoia. Safest upgrade process is to have an external Time Machine backup before attempting. Doesn't matter how you update .. via Recovery, USB installer, or App Store version. Having backup is safest.

2. Which recent OS can my iMac reliably & reasonably handel? & is it worth/necessary for me to add 8 GB ram (for 16GB total) to handle 'modern' (lol) OS. I am thinking on resting this baby on Sonoma but not sure.

Yes, add 8GB RAM, if not more.

How much free space do you have on your internal storage?

 

[MarE66]

Latest macOS version your model can run is macOS 15 Sequoia. Safest upgrade process is to have an external Time Machine backup before attempting. Doesn't matter how you update .. via Recovery, USB installer, or App Store version. Having backup is safest.

Yes, add 8GB RAM, if not more.

How much free space do you have on your internal storage?

THanks for your reply,
I have a Time Machine external back up. I have 340GB free space on internal storage. By 'safe' I meant will my imac 2019 be able to run Sequoia reliably given my current/original config. & even if I add 8GB ram?
As far as OS update goes..can I jump right to Sequoia from Mojave.
For RAM - I currently have 2 4GB cards is it OK to just add a single 8GB card.

 

[Bigwaff]

As far as OS update goes..can I jump right to Sequoia from Mojave.

Yes, but some of your installed applications may not like it.

For RAM - I currently have 2 4GB cards is it OK to just add a single 8GB card.

You will have to look that one up on Apple support site. RAM is typically installed in identical pairs.

 

[LeVan]

Yes, but some of your installed applications may not like it.

You will have to look that one up on Apple support site. RAM is typically installed in identical pairs.

Bigwaff is right, usually identical pairs is standard, but two different capacity pairs is also possible, and sometimes necessary if an identical pair can't be found, but in any case get two identical chips with the exact specs shown on the following page (info on the RAM you need). <https://support.apple.com/en-ca/108317>
It says it is best to use chips with the same capacity, but you can also add 2 8GB chips for a total of 24GB.
A good app to have is the small free Mactracker app, available on the Apple App Store, which will give you details about all the Apple models ever made.

 

[Fishrrman]

"I am also planing to buy a new iMac 2024..."

My advice will be different.

Put your money towards something new, and NOT the 24" iMac. I predict you'll soon find yourself "constrained" if you "move downward" to a smaller display.

I'd suggest an m4 Mini, or perhaps even an m5 Mini when they're released (perhaps later this year).

RAM: At least 32gb.
SSD: At least 1tb.
Display: either a 27" 5k, or perhaps even a 32" 6k (starting to come onto the market, but don't pay the ridiculous price for the Apple). I use a 27" 4k right now with my own m4 Mini and am satisfied with it, but considering 32" 6k before too much longer).

That's my opinion and I'm stickin' to it !