re: How to make $300k arbitraging credit card points and then pay zero taxes on it

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Do I need to get a personal Chase Sapphire and just start running some personal expenses through it (groceries, gas, etc.)? Then just stick to Chase only? Hotels and Airlines will be main uses for points. But I think AMEX to Hilton transfer is good too? I don’t know. I don’t keep up with where and how to redeem as well as I should because I’m usually just cashing out.

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I have a personal Chase Sapphire Preferred and was able to transfer my business Ink points to that account. To transfer points you need a Sapphire Preferred or Ink Preferred card. I like Chase points because they have more airlines I like. Amex points are good but they have fewer airlines, mainly Delta domestic. Amex points can be used for KLM/Air France but these are rarely good deals.

I would not transfers Amex points to Hilton as the value is less than if you use for airfare. I have an Amex Hilton and that is a better way to build Hilton points (you get complimentary Diamond status which is nice as well).