We present a comprehensive ablation of nine finite-sample bound families for selective prediction with risk control, combining concentration inequalities (Hoeffding, Empirical Bernstein, Clopper-Pearson, Wasserstein DRO, CVaR) with multiple-testing corrections (union bound, Learn Then Test fixed-sequence) and betting-based confidence sequences (WSR). Our main theoretical contribution is Transfer-Informed Betting (TIB), which warm-starts the WSR wealth process using a source domain's risk profile, achieving tighter bounds in data-scarce settings with a formal dominance guarantee. We prove that the TIB wealth process remains a valid supermartingale under all source-target divergences, that TIB dominates standard WSR when domains match, and that no data-independent warm-start can achieve better convergence. The combination of betting-based confidence sequences, LTT monotone testing, and cross-domain transfer is, to our knowledge, a three-way novelty not present in the literature. We evaluate all nine bound families on four benchmarks-MASSIVE (n=1,102), NyayaBench (n=280), CLINC-150 (n=22.5K), and Banking77 (n=13K)-across 18 (alpha, delta) configurations. On MASSIVE at alpha=0.10, LTT eliminates the ln(K) union-bound penalty, achieving 94.0% guaranteed coverage versus 73.8% for Hoeffding-a 27% relative improvement. On NyayaBench, where the small calibration set makes Hoeffding-family bounds infeasible below alpha=0.20, Transfer-Informed Betting achieves 18.5% coverage at alpha=0.10, a 5.4x improvement over LTT + Hoeffding. We additionally compare with split-conformal prediction, showing that conformal methods produce prediction sets (avg. 1.67 classes) whereas selective prediction provides single-prediction risk guarantees. We apply these methods to agentic caching systems, formalizing a progressive trust model where the guarantee determines when cached responses can be served autonomously.