Confusion and Concerns About Our Front Office

I don't understand why our front office doesn't just simply sign every key free agent for the veteran minimum. Why overpay them by tens of millions? If I were the front office, I'd simply sign everyone.

And why do we only have one 1st round pick? Is there a reason Caserio hasn't traded the 23rd pick for the 1st pick in the draft, our 3rd round pick for the 3rd pick, so on and so forth? All of these moves seem so obvious to me.