Welcome aboard!
We are not all crazy here, but some are crazier than others. haha
Seriously though, I hope you become crazy but selective plant lady. Always check for pest and diseases when introducing new plants into your collection. This will save a lot of stress, anger and energy down the road.
There are no such things as beginner plants or difficult plants.
If you can provide proper conditions, anything will grow. Problems arise when people want to have something pretty or unique without being able to provide (or realizing) the right conditions for them.
Now, with your nice and cool winter temperature (I wish I had it!), you can grow beautiful colorful and wonderfully fragrant Miltoniopsis if you like such things!
There are many colors to choose from, and all benefit from cool to cold winter conditions to do well long term, hence most warm indoor grower are not that successful with this group.
There are also many paphiopedilums ( People either love them or hate them lol) that will do great with your conditions, but perhaps slightly more shade than full blast afternoon west sun. You mentioned trees providing shade, but I have no idea how mush shade. It might be perfect or may be still too bright for these.
I would recommend paphipedilums in the section parvisepalum. These are the ones that less people are repelled to, it seems, and majority of them do well with cool winter conditions with warm summer.
So it fits the bill for ya.
Then, consider Stanhopea if you like strange flowers with strong scent.
You will also do well with certain Dendrobiums like nobile hybrids and other similar groups.
Den. kingianum might need cooler conditions than what you have, but you can try and see how they respond if you find them good to your taste.
There are just so many that will do well for your conditions.
You will have to narrow down by your preferred colors and other factors like, do I like spotted or oddly marked flowers or clean cut looking ones?
Do I want fragrant flowers? Stinky ones? Some people do, believe it or not. but me, though. haha
Are sensitive to strong scent? some flowers can give you headache in the room.
Do I want large plants? small plants? hanging baskets or neat pots?
These will help you narrow down the list of what you want to have.