Yea, thats what I meant. Example - I combine the TY Checking account (51k Taxable points) with the Prestige account. Then I redeem 37k Taxable points for $592 in value today. At this point, if I redeem any more points in that combined Prestige account for a flight, I would get a 1099 for going over the $600 line. Then, if I waited until mid October and downgraded the checking account, I would have 90 days to redeem the residual 14k Taxable points. I wait until January and then I can redeem those remaining 14k points. If the 14k points will be worth 1.6c/pt on AA, that is $224 of value vs $90 in extra checking account fees so it could be worth it. Does that make sense?

Now also... what if, after redeeming 37k points ($592) in the combined Prestige account, I transferred points from that combined Prestige account to an airline instead of redeeming for cash value? Do they tack on a value for that for 1099 purposes? Or is that okay since a transfer will draw from non-Taxable points in the combined account?