Log in to each account, set the date range, and download CSV (not PDF — CSV is matchable).
Email receipts, phone photos, app exports — dump them all in a single folder before matching.
Sort both by amount and date; match in descending order of value so the big items clear first.
Use a fixed category list (max ~12 categories) so month-over-month reports stay comparable.
Mark anything ambiguous — don't guess on tax-relevant items; send one consolidated list.