I wouldn't be surprised if cashback wasn't a good option as it might create a taxable event if transferred from business to personal.

I'm sure it depends on the particular structure of what business is involved, but the position that it's the clear winner doesn't seem to be backed by a full analysis.

When you think about it, with $1m in spend, there is a good chance that cash discount might be the way to go. It would not be unheard of or unreasonable to expect 3-4% cash payment discount so the vendor does not pay credit card charges. In fact it's only travel that I can think of that would justify spending so much on a credit card... but welcome to be enlightened on other types of spend that can reach that level that you would not be able to easily negotiate cash discount on

Some vendors are willing to offer a discount for invoice versus credit card billing, but there are two issues with the 3-4% figure you suggest. First, large scale merchant accounts don't pay nearly that much in fees, so they'd be overcompensating at that discount level. Second, invoice billing brings on new risks that need to be accounted for.

Two examples of business spending that can rack up huge card charges and doesn't need to be related to travel are eBay and Google AdWords.

Problems with discounts and/or cash back cards
 

Great feedback on this thread.

The cash back plans are a good option after racking up points on a hotel card, SPG is on the way. However, this is a Business card and the cash would come back to the business. If so I can't simply take the money out of the corporation, there would be a taxable transaction. This is another point I never see come up. For the spend I have annually on my Business card these award programs are a great tax free benefit, the taxable cash equivalent is much higher than that of the award itself if you stop and think about it.

Secondly, I already get early pay discounts from the larger vendors I am using my AMEX to pay. Once again though, any additional discounts would come back to the corporation and not available for tax free benefits.

What does OP mean by "vacation type properties the pickings are not extensive?"

It's 1am here, so i'm tired and maybe I missed where this was asked...

But I think some important questions for the OP are.... where do you like to go on vacation, and what types of properties do you normally stay at? How many nights per year are you thinking you'll stay in hotels?

If I've read correctly, you don't travel internationally, and you want a card that's not an AMEX, because you already have one... correct?

Correct
 

Already have 2 Bus. Amex's. Vacation preferences would be 5-7 nights, high end resorts in Caribbean, Costa Rica, perhaps French Polynesia, Bermuda and/or Bahamas.

How is that not traveling internationally?

Tahiti will be well served by getting a Hilton Surpass as Diamond benefits in Bora Bora and Moorea will be pretty good. Here’s an idea, wander over to Marriott, Starwood and Hilton reservations sites, put in your dream locations, and pick the hotels that get you excited and apply for credit cards accordingly.

One thing that might not be obvious from looking at reservation sites is that many (most international) Starwood properties allow you to use points for dinners, spa appointments, etc. Sometimes the redemptions aren't the best values, but if you have a boatload of Starwood American express points, what the hell.

Jailer
 

Thanks for the input and suggestions.

It depends on the card, but in general, no. Many, if not most, cash-back cards provide the option for a paper check rather than a statement credit. Discover, Chase, Citi, and various AmEx cards all provide paper checks. The Fidelity cards deposit directly into a savings account, so as with paper checks, they do not affect your credit card bill. Therefore, in most cases, the business check is written on the full amount, and the cash-back is processed separately.

Now that may be true. The IRS does not tax (or require reporting of) card cash-back because they consider it a form of post-purchase rebate. If the rebate is funneled to a personal account based on a business purchase, however, that might well count as personal income. (In practice, the expense required to police this sort of thing likely far outweighs any income the IRS would hope to gain, on average, and since the IRS does not require reporting of card cash-back payments, then assuming this is even a problem, the only way it would be caught is with an audit.) Disclaimer: I am not a licensed tax professional.

(I note that the above situation is exactly akin to an employee using a personal cash-back credit card for reimbursed business expenses, e.g. business travel... the employee reaps cash-back rewards with effectively no out-of-pocket expense, which may therefore technically be taxable income since it's no longer a rebate on the employee's out-of-pocket expenditure. However, as above, policing this is simply not feasible.)

I would recommend several cards

American Airlines - as has been mentioned previously - use it until you earn a lifetime status of Gold or higher.

Delta - use the business platinum card until you top out your MQM - or the Reserve card if you find that your leisure travel will make that card's cost worth the expense.

Continental/United - may as well keep your options open with the major airlines.

Hilton Surpass - spend enough to get Diamond status.

Marriott or ICH cards if you expect to stay at their resorts. Likewise Hyatt.

SPG Amex is the Gold Standard for Frequent Flyers. Not always to use at SPG hotels, it can be converted to other programs.

Many of the cards above are no fee or low fee. The value of the points earned will be huge for yourself, your family, friends, employees or business partners. Lots of things you can do with the points earned on a 7 figure annual spend.

Good luck!

You may be right, but it seems to me that if you get, say, a $20,000 personal cash refund/rebate on $1,000,000 of business expenses and do not report it to the IRS that this would be tax fraud. Sure, the IRS may not fish for these kinds of transactions, but just how would you explain not reporting $1,600 per month from Citibank, or whomever? I’ll just take the points and miles, thank you.

A number of years ago a scheme whereby NBA referees exchanged their first class tickets for coach and didn’t report the income resulted in firings and prosecutions. A high school acquaintance who is a NBA ref shared that he considered it but it seemed to him like income, so he didn’t bite. Besides, he preferred to fly F/C and get to the games in halfway decent shape.

I would go for Fidelity Amex if possible to use personal card on business expenses which will help you to grow your IRA, if chosen. All tax free.

Well, it wouldn't be tax fraud if the IRS has issued a blanket statement exempting CC cash-back from taxes, much the same as was done with FF miles. Sadly, I don't know the exact specifics of the IRS position on this, so I don't know whether it's simply exploiting a reporting loophole (i.e. probably illegal but hard to trace) or whether there's an official position exempting all CC cashback, business or otherwise, from taxation (i.e. legal, like miles).