I'm not kidding zr when I say I know just how you feel about the oracle series.
My story starts out almost just like yours. Way back when I only had Oracle of Seasons my family and I use to take long trips across Australia to visit relatives. These long trips involved driving from Perth to Adelaide: a 3 - 4 day trip of around 2 and a half thousand k's. To set the scene, the largest stretch of this journey involved crossing the Nullarbor plain - one thousand k's worth of red dirt, yellow grass and hot weather.
We made this journey twice and each time the go to games that I brought to keep me busy were Pokemon Gold and Oracle of Seasons. I'd pretty much exhausted Pokemon Gold by the time we made the first trip (I had a level 99 Feraligatr called Bluey which is a whole different story) and so for the majority of the trip I played Oracle of Seasons. I have no idea how many hours I put into that game during the first journey, but two things that are for sure is that it was the first Zelda game I ever beat on my own... and that it was my favourite.
The second time we made the journey must have been around Christmas 02/03. I did the same thing this time; brought Pokemon Gold, my Gameboy and Oracle of Seasons. I have some of my best memories from that holiday. I didn't know at the time that this holiday would be the last time I saw any of my family that lived there again for a long time.
2010 was the first time I went to Adelaide again since that Christmas holiday so long ago. In that time I lost my Grandad to cancer while my Granny also suffered with bowel cancer. The only reason we went there when I was younger was because my Dad got free petrol on the company car that we travelled in. We didn't really have the money to fly over often so it was only my dad that ever went. I cant tell you how weird it was being in my grandparents house again after all that time.
I know now what it is about Seasons that makes it my favourite Zelda. Its the wave of excitement that hits me while playing that tells me I'm going to see my family. Its the memory of being a small little boy in the middle of the Australian outback. It's pretending I'm link in a car that is my horse while travelling across the fields of red dirt that I'm out to save.
Its honestly been so long since I last booted up the game that I'm starting to second guess whether I should download it and play it on my 3DS. Maybe I should just get out my Gameboy colour and play it on there oldschool. I don't know.