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The word he would use to describe himself was "expendable."
If he had to restart his timeline over and over, a hundred times, a thousand times, if he had to start his life over every couple of months, leave behind everything he knew to go live on some island, if he never got thanked, if he had to break countless time regulations, that was just what was going to happen. It's for the good of the mission. What're you gonna do?
He couldn't even say it was for someone who would do the same for him. And it was nothing against Cavendish- heck, he'd never ever say Cavendish didn't deserve to be saved, in Dakota's mind he did, he absolutely did, no questions asked- but Cavendish WOULDN'T do this back. He just wouldn't, it was the truth.
It was the way Cavendish thought. He didn't think of himself as expendable, he thought of himself as a failure.
Dakota knew if HE were ever on the receiving end of an AC unit falling from the sky, or the front of an 18-wheeler, or a broken safety rail, or any of the many, many ways Cavendish managed to die, Cavendish wouldn't go back in time to save Dakota, not because he didn't care, but because he wouldn't want to mess it up any more. Cavendish would never break Bureau protocol by going back in time to save someone like that. He'd also have the foresight to know there would be a double of him afterwords, and then what? Send them off to an island where they'd never be seen again? Don't be absurd! ("Absurd" would be the word he'd use, Dakota could picture it perfectly.)
Oh, he'd do something; he'd quit. He'd blame himself, he'd quit the time travel business immediately. Maybe he'd take up piano again. Maybe he'd actually get to play piano as a career, or do that...thing where you wave the stick around in front of the orchestra, maybe he'd be really, REALLY good at it. No, of course he'd be good at it. He'd be so good he could do it as a living. He'd be successful. He'd settle down and be given something Dakota could never, ever have anymore- a normal life. And maybe he'd forgive himself. Maybe he'd stop mourning. Maybe he'd start living more days where he DIDN'T think about Dakota than ones where he did.
But he'd never have to do that. He shouldn't have to, if Vinnie just kept being careful, kept staying alive. If Vinnie kept calm in the face of danger, if he continued to not participate too much in their missions so it wasn't HIM getting hurt, if he just kept his head, kept calm, don't get hurt, don't get hurt, he'll die again if you die. Don't think about how he sounds when he screams, don't think about how it looks to see him get crushed, smashed, blown up, shot, don't think about how his blood smells, don't think about how even though you've smelled it exactly 53 times now it STILL makes you gag because you know where it came from and why, just don't think about it, it's for the good of the mission, for the good of the mission, for the good of the mission.
Vinnie was expendable. It's no skin of his back if he has to keep resetting his life.
The question wasn't why is Cavendish worth all this trouble. The question was why did Vinnie think he was worth so little to the world that he didn't mind bearing the weight of this all on his shoulders?
When Milo asked him this, he was old enough to be asking these kinds of questions, because he was old enough now that he noticed things. He was always smart, but his later highschool years showed him to be a very intelligent, insightful, and attentive kid. Dakota couldn't help but love that little sucker. But he noticed things Cavendish didn't. He noticed how Dakota always seemed to know to prevent danger, and when jokes about his low self-esteem and since of self-worth became too frequent and too...not joking.
Dakota told Milo the process, and Milo asked him something he himself had never thought about before (because Milo was smart, he was so smart, he could look at Dakota and see right through him,) which was why Vinnie thought so little of himself that he took on this burden. Dakota was expecting "Why is Cavendish worth all this trouble?" not "Hey Vinnie, tell me why you hate yourself so much!"
Okay, he didn't phrase it like that, but that was how it felt, and something about those sweet little brown eyes just made you want to spill your guts out (don't think about his guts spilling out-) and tell him everything. He was so sincere it was sickening. Dakota had responded by shrugging it off and laughing, what're you gonna do, but Milo pressed on.
Dakota didn't...HATE himself, he didn't think, did he? He was just...he didn't know. Expendable. Everyone was, really, in the grand scheme of things. Now there was a concept, "the grand scheme of things." The mountain range of time all time travelers floated above, seeing time not as a line you traveled on, moments fleeting and never coming back, but a series of moments that happened all at once and not at all. He just wasn't...special. He didn't contribute anything to this world of note. Why was HE the expendable one and not Cavendish? Dakota didn't have an answer. He wished he did, because Milo was staring at him with those eyes that demanded you be honest and sincere, but it wasn't something he ever thought too much about before. When he did, it just made him confused and upset, so he just didn't. Push it to the back of your mind and repress it, that's the healthy way of doing things.
Milo had hugged him when he had tried and failed to explain why he thought it was okay that his life was put underneath someone else's, to the point where he'd constantly have to clean up a mess he didn't make and never ever get thanked for it, and why he thought that was okay, and the hug confused Dakota more than anything. Milo told him he was brave. He didn't say anything, but he didn't think he was. A brave person wouldn't peek into Cavendish's apartment window every now and then to make sure he was safe in bed. A brave person wouldn't still feel the need to cry when he thought to hard about what Cavendish sounds like when he's slowly, slowly dying. A brave person wouldn't hide his doubles away on an island to live out the rest of their lives in silence and die.
When he dared to let that little spot in his brain he kept repressed come out briefly and dwelled on it, he probably had some messed up ideas about his self worth. He probably had some messed up ideas about what it meant to be a friend. He probably had some messed up ideas on give and take, and he probably knew he'd spend the rest of his life giving and giving and giving and he'd never take.
But hey, it was Cavendish. What're you gonna do?