Where do I start?!

Trying to tackle an actual yard plan (has been in the family since being built in 1936)- over the past 3yrs I have redone some things inside the home and now want to focus on the outside. I have installed a patio at the bottom of new stairs leading from a new slider in the dining room. I also updated the fence last year from wire to white PVC and removed some woody hedge and random growth along the the property lines.

Goals:

• Conversation/Outdoor dining: would like to make a lounging conversation area and/or an outdoor dining space. Not sure if both are possible.
• Small Play area- Child/dogs: would like a small play area ( ideally either grass or open to fake grass due to being shady area re: GIANT oat tree and grass has ALWAYS been difficult to grow) for small child and 2 dogs.
• A reading nook for relaxing and enjoying being outside.
• More privacy from back neighbor who has full view of my yard from their deck (I did put a 6ft fence on the back of the property but due to the slope it really didn't do anything unless you are RIGHT up to the fence) They have a small maple tree that helps a little when the leaves come in right on the line, and my own Oak tree also shades a bit- but I still feel like I would like to remove the prying eyes.
• New to Gardening: Trying to get more into gardening but specifically I really want to keep the multi-generational family irises currently planted along the fence line in someway on the property (also want to bring back to life 2 scraggly rose bushes- but feels unfair to call them "bushes" its 2 sticks a piece that flower haha)

Issues:

• water from driveway tends to run onto the patio and pool in top right corner. (I am hoping to redirect that water in a separate project)
• dogwood tree in middle of yard- can be removed or stay
• someday will need to replace the old garage
• there is also a slight slope from the back of the property to the patio- but no water run off that direction- surprisingly and amazingly
• New England- so hot summers and snowy winters (or lately into April snow!)

Yard size: 32'x 46' ( I did extend the fence down the right side beyond the backyard for what I had hoped to be a dog area- that is an additional 9'x21')

Budget: $8-10k

I don't know what to focus on or questions to ask if I connect with anyone.

Suggestions or ideas? (I am also hoping to get new furniture that will better suit the space!- I am NOT afraid of color!)