I think once you break the seal on Souls games they somehow all seem easier. The first time I ran at O&S it was on the Switch and I was at it for about a week, must have been dozens of attempts solo, and I didnt have Nintendo online to get any help from a summons. I played the whole game without any online features so I didnt even really realize it was an option.
The first time you open a shortcut is a moment though, especially when it then keeps happening again and again.
After Sekiro came out and I loved it I picked up the other games and played them. I did DS 2 last and it was my least favourite, but that can also be because I'd played a lot of Fromsoft games all in a row and I was a bit tired of the style.
At the time I played them all before Elden Ring I would have said DS3 was my favourite, people seem to consider it the most linear and I can see it, but it didnt bother me. The combat feels slightly smoother somehow and the bosses were all pretty good, IMO unlike the first two games which both had some bad ones like BOC or Triple Gargoyles which are frustrating rather than well designed.
Havent ever beaten Manus in DS, or done a lot of the DS2 DLCs which people say are the best parts, and I didnt finish the Ringed City DLC in 3 either. Probably saving it for my retirement in about 75 years at this point though.