updating 2019iMac to 10.15

[macj3]

I have a 2019 27" iMac, 3.7 i5, 8Gb ram, 1tB SSD. Running Mac OSX 10.14.6. The new Tax program needs 10.15. I was wondering If I should just "jump up" one OS from 10.14 to 10.15 or go further? Maybe all the way to macOS Monterey? Will the newest macOS Monterey play well with my 2019 iMac? or just go to Catalina (10.15) or Big Sir (11.6.2)? Would it be best to jump incrementally or just go up in one big leap?
Have an iPad running iOS 12.4.9, will that be effected?
Thanks in advance for any replies!

 

[tensixturtle]

I am sure your iMac can handle going from Mojave to Monterey at once, and I am sure that Monterey would run fine. I think iOS 12 also works with Monterey. However, I don't know how picky you are about operating systems, but there were some nice design elements in the macOS 10 line (before Big Sur) that I liked. That is why I purposefully keep some of my computers running older operating systems than they can technically handle. In that case, since it is harder to downgrade, I would just update to Catalina. Otherwise, I would go with Monterey if you don't feel strongly about certain aspects like that.

 

[macj3]

Thank you for your reply. I'll just make the small step to Catalina hopefully that will be good until next year!
Thanks again.