What I'm looking for is a cheap ($25 or so) Visa/MC that I can get and then subsequently top up online to around $500 or so. Does that exist?

Merchant is willing to split but I don't want to pay NYS and NYC sales taxes twice which I would if I used your method.

Unless NYC is different from the rest of the US, gift card sales are not taxable for the very same reason - to avoid double dipping on sales tax,

About how much do these cost? Is there a max amount, like $500?

Noob "If you were in my situation" question. Large spending.
 

Uber-noob here. I really appreciate all advise and opinions. Here is what's going on and what I'm looking for:

I have a small business that charges about $10,000 per month on credit cards. I currently use a Amex Plum because of the 1.5% early pay cash back and the 60 day terms. I also use a Citi Premier Pass (Thank You) for some purchases (I was digging the points for flight miles perk). Unfortunately, neither card converts to FF miles. I would love to make a switch to one card and rack up some serious miles.

I don't particularly fly a lot for business, mostly leisure. When I fly, I unusually fly out of Savannah, Georgia. The major airlines that fly out of SAV are United, Delta, and US Air. I was reading about the new United MilelagePlus Club Card and the 1.5% for every $1. I could care less about Club access in airports and rarely stay in hotels or rent cars. The biggest thing I want to do is rack up miles as quickly as possible. Upgrades to business/first class would also be awesome if I can reach some sort of level. Again, I don't fly much, so the traditional miles or segments to reach a certain status probably won't work for me.

Lastly, I do a lot of business with China and wire about $15,000 to $20,000 per month using my Bank of America business checking account. Are there any options out there to get some miles from these transactions?

Thanks again in advance!!! Already learning so much on here!

I think it's easiest to get the bonuses to get lots of miles rather but you're in a great position. 1) Get chase United airlines card with 50k. 2) Get Chase sapphire preferred mastercard 50k 3) get chase ink bold 50k You can get all three cards and meet the bonus w/in first month. That's 150k miles. Then transfer Ultimate rewards miles to United for 150k miles. Then use one of those cards for your purchases.

A year or so ago AMEX had a program where you could get Membership Reward Points for international money transfers. I don't know if that program still exists.
You should look at frugaltravelguy.com, both because he has lots of good info on getting FF miles and because he primarily flies out of SAV.

I think Chase will not allow to get three cards within one month.

What cards you should apply for depends on where you want to go. What are your dream trips?

Thanks for all the feedback so far! My fiancé and I love to travel to new places, and we have gotten to the point where we have seen most of the MAJOR cities in the US, so we would want to go to places domestically such as Aspen, CO or lots of places internationally, such as New Zealand and Egypt. I have been using United's reward travel search engine playing around, and it sure seem like a HUGE perk to be able to pay some more points and get first class (especially overseas). Right now I am torn between the Capital One Spark card for 2% cash back on everything, or one of the United cards (Explorer or Club). I estimate my yearly charges around $200,000. However, my business is growing very quickly and this number could be at $300,000 by the end of the year. That would be a crapload of miles, especially with the United Club card!

Why choose? Get both. The best way to rack up miles in this game is diversification. Consider signing up for one card per issuer every 3-6 months (depending on your tolerance). It seems like you should easily meet the spending requirements and then you can have 1-2 main cards as appropriate. The only card I would not sign up for is the capital one ventures card as if they bring back the match my miles promo next year you would likely be well poised to take advantage of it. Consequently, if you are going to rack up a lot of spending on 1-2 cards, make sure at least one is not a capital one card.

Also get the spg Amex (biz and personal). It's one of the best for non categorical spendnand has great redepmtions

Do any of your purchases qualify for category bonuses? If so, look at those cards for sure.

The advice to diversify is extremely important. It's terrible to sit there with a million miles in a program that you cannot use instead of 250K in each of 4 programs (illustration for simplicity's sake).

If you lived in a Southwest city, I'd urge you to go for their Companion Pass for unlimited free domestic trips for your fiancé'.

I'd recommend considering the Hilton Amex because that will get you to Diamond with $40K spend in the calendar year. Diamond can be worth a decent amount, especially internationally, and it appears you might be able to use it. The 6 points/dollar categories are also a worthwhile way to get points, sometimes.

Chase BA Visa gives you a companion ticket with $30K annual spend. That could be worth a lot, depending.

You might also inquire of your suppliers if they'd give you a discount for cash. That could be worth more than any CC points/miles.

Finally, you should attend one or more get-togethers with knowledgeable people. Techniques get passed around word-of-mouth that never/rarely make the internet.