Huge thanks to you all for helping me to figure this out!
I'm not 100%, but based on what you all were saying, we decided to drop that random first night in LA 5/21, and moved our WB Tour to the following week 5/28.
We now have 6 nights at DLR, but the first day will probably be just getting acclimated and not a park day. The next 5 days, we will be hitting the parks, but we are typically, "rope drop/mid-day pool break/back to parks at night," people, so we will have some time to relax in there.
We'll still check out on May 27, but we'll rent a car at Paradise Pier and head up to do Santa Monica, Venice, etc.
May 28, We'll do the WB Tour at 10am, then maybe visit Rodeo Drive (visit…not shop!), walk of fame, Griffith park, etc.
Just FYI, I sent this whole thread to my DD and told her I really needed her to weigh in on what she wants to do. Her thoughts are Santa Monica/Venice, Rodeo Drive, WB Tour, and then what she would really like to do is just find some cool shops to poke around in. Her friend goes to Chapman College out there and will have to tell her where to go. She'd rather wing it and as a planner, there's no way I'm doing that! The only other thing I might make her do is Griffith Park/Griffith Observatory at sunset maybe. I'm guessing along the way we might also check out the Walk of Fame and Chinese Theater. I don't think that'll take very long though.
I'm debating between getting a hotel at Universal City for both 5/27 and 5/28, or do I just book there for 5/27 and then move closer to the airport for our last night, return the car that night and shuttle to the airport on 5/29? Our plane leaves at 7 am and I guess I don't want the stress of returning the car that morning so I might split it.
Again, thank you to everyone who bothered to read this and for all your helpful tips! The logistics of this trip stresses me out a little, as I'm so used to WDW and just knowing everything