The tall trees or shrubs would have to go at the top of the slope by the sidewalk… but I think if we just plant evergreens there it will look funny. Maybe i’m overthinking it

Ideally you'd terrace the front yard with retaining walls. You could then layer plants so that you have more privacy. You coud also consider a low fence with some shrubs. It might be worth it to talk to a local garden center (not big box) and see if they do design work. Often they'll do a design for a modest fee if you buy plants from them.

Hedge planted next to the sidewalk. Or a fence.

Don't avoid deciduous shrubs because you don't think they will provide privacy during the winter. A lot of them are twiggy enough to do a decent job, and usually the privacy needs aren't as great at that time.

You don't say where you are, but around here a lot of people use
forsythia for privacy hedges. It's cheap, indestructible, deer
resistant, can be pruned, can be not pruned, can be hacked back if you
change your mind about pruning, and best of all, is thick at ground
level.

Forsythia would certainly work if you're looking for something very easy and aren't looking for more seasonal interest. And it would establish fast. Me, I'd want a mixed shrub border. And that's what I've started in a somewhat similar situation.

IMO you need a fence anything you plant there will need to be evergreen or it will not do much and all plants grow so the green wall will eventually appear . a nice fence with soamce nice landscaping on your side will be attractive to you and help the dog not be able to see everything but he will still bark since his hearing is the other issue.