1. Will you connect your bank?
Connecting accounts is the only way an app can discover subscriptions you have forgotten, and it is the single biggest privacy trade on offer. Rocket Money, PocketGuard, and Copilot Money require it. Subkept, Bobby, Chronicle, and SubBuddy never ask for it, at the cost of adding subscriptions yourself. Neither answer is wrong, but it is the decision that eliminates half the market.