There have been about 4 cycles of recruiting so far. I'm currently competing against a SIM AI D1 school for a recruit (D- Prestige; I'm at a D3 school with A+). The SIM is currently at "Very High" interest with a scholarship, and I'm about 60% towards a scholarship offer. Is there any way I could win this battle, or should I just give it up?

You can win it, but you need to go be willing to go all in as early as possible and in the same cycle. I’ve bumped sims to VL before by doing this but you need to be early, able to give max visits, promises, and do it all in one cycle. It’s generally a pretty big risk especially because D1s can still come later.