Welcome to the board!
The short buzz doesn't look too bad and you have nice beard coverage. If you aren't ready to go all the way yet, that doesn't look too bad, but maybe you could try a shorter, no-guard buzz to start? I think you're being harder on yourself than you have to be. I'd grow out the beard a little more to detract from your current hairline. But down the road if the receding continues, you might have to look into wet shaving, but I think you're okay where you are now (unless you just want to try the wet shave).
Pictures look awesome, you carry that look well. There is no need to hide under a hat. If you wanted to try sly, given the length you are currently wearing, if you didn't like sly you rally would not have to wait long to get back to your current style. That said if you do try sly, remember the 30day rule, it does take a while to get used to any new look
at your age in college I kept my hair as short as yours by desire. Sure I got kidded - my nickname was cueball. I never wore hat. I gained self confidence however realizing I had the courage to be different.
WELCOME to the forum!!
I think you look great with your hair buzzed short like it is now. I too think you could go closer and still look awesome. Don't hide under hats. Your head and face with the beard look great together. Do what makes you happy but just know that your look is great as is. If you want to try shaving your head I say go for it. If you aren't happy you can grow it back out to the current length in no time but I think you will love it once you do it! Best of luck man in whatever choice you choose!