IRS treats points/miles earned on personal purchases as rebates — NOT taxable income.
Rev. Rul. 76-96 + IRS Announcement 2002-18: credit card points, cash back, and miles earned on personal purchases are treated as REBATES (basis reduction), not income. NON-TAXABLE. Exception: sign-up bonuses given WITHOUT a spend requirement (e.g. bank account opening) can be 1099-INT. Also: MS profit theoretically taxable but not enforced. Business purchases: rebate reduces deductible expense.
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Buy Visa gift cards → liquidate to money order/deposit → earn points at ~1% cost.
$695 fee offset by $1,600+ in credits if you actually use them — net positive.
Have status at one chain → status-match to Hyatt Globalist, Marriott Titanium, Hilton Diamond.
Complete 30 Hyatt nights/yr for Globalist — suite upgrades, breakfast, 4pm checkout worldwide.
Earn 135K qualifying points → companion flies free (just taxes) on every SW flight for ~2 yrs.
Redeem 90K–130K miles for $6K–$15K international business seats.
Deduct real business travel — combine with personal side trips at 50/50 rule.
Time Chase applications first (5/24 rule) before Amex/Cap One that don't have the restriction.