Help! I messed up.
 

Ok. So here's the deal. I consider myself an part-time, amateur MSer at best.

Last week I went on a small CC app spree. I now have 2 cards that I really want hit the bonus sign up offers on.

Capital One Venture (Visa). 50,000 points with $3000 spent in first 3 months.
Hilton Ascend AMEX. 100,000 HH points with $3000 spent in first 3 months.

In the past, I've always used Plastiq to just pay my mortgage and that was it. Well, I signed up for both of these cards without being aware that you can't do that with Visa or AMEX any more. So that sucks..

So, now I'm trying to figure out how best to hit the bonuses. Not gonna lie, I really hate the gift card thing. It just seems so risky. But if that's how I have to do it, I'm game.

I'm reading through the gift card threads now trying to catch up on the current best practices but if anyone has any tips for me, I'd sure appreciate it. If GCs are my best option, I'd love to wind up ultimately paying my mortgage if possible (WF Home Mortgage).

Thanks.

I'm kinda thinking about buying GCs from GCM and loading them onto my apple pay cash card (which is managed by green dot). Hold it there for a while and withdraw to my checking account. Does that work? Has anyone tried this?

In what increments should I buy GCs so as not to upset Amex or Cap One?

The quick and easy way to do it is to convert those GC's into WM MO's and be done with it. Or just purchase retail cards you know you will use like Target, Amazon, fuel cards, etc. I don't think I've ever had a problem with retail cards and the only time I've had a problem with VGC's is if they are held for too long. Get rid of them within a day or two and you should be fine. Or if you want to do it the natural spend way, see if you can prepay some future insurance, phone, cable bills, etc.

for this card, best NOT to buy GCs from GCdotcom or GCM or else the axp rats will make sure you don't get your points. Read or re-read their terms on what qualifies for the required spend so you know.

This, with emphasis on the GC-to-MO part, also consider WM BP. With all due respect, $6k of spend/liquidation is chump change, you could do it on your lunch hour, depending on where you live.
Don't worry, be happy.

Pay your phone bill 3-6 months in advance
Pay your car insurance premium in advance
Pay your cable bill 3-6months in advance
Pay your water/electric bill 3-6months in advance
Buy grocery store gift cards (where ever u normally buy groceries)
Buy gas gift cards.
Buy visa gift cards from office depot/max /staples when they offer 10-20dollar off /rebate which is usually in their Sunday ads every 4 weeks
Buy Amazon gift cards.
This isn't manufactured spending though.. more like advanced spending but works fine.

GCs work fine for Hilton Ascend card spend.

Pretty much this. Got any high-dollar bills coming up like home/auto insurance, home improvements/repair, season tickets, etc? Not MS, but can quickly get you that minimum spend in. Otherwise, it's the GC route, with some other regular spending thrown in.

$6K is a walk in the park. Go to a Simon's Mall if you have one near you, fill out a sheet of paper for 12 $500 VGCs. Walk into Walmart and get some money orders. Put them in your bank account the same day. Pay off your two credit cards when they post into your account.

Enjoy your points.

Recent reports say SimonGCs (online or bought at the mall) no longer count for AXP min spend requirement.

OP, SimonGCs post as BHN Giftcards which makes it very easy for the rats to see what you've bought. Caveat emptor.

Cannot agree more with Mamibear, it's a good idea to stay away from SimonGCs, GC.com and GCM for Amex minimum spend requirements. It's too risky to play around with MS with an amex sign up bonus.

You're right I missed that he got an Amex. Don't buy from Simons for MSR.

Tax payment
 

If you can float it for a month or two. Make 2017 tax payments on pay1040.com and file your return and claim a refund. Only works if you did not file yet. I overpay on Jan 15 every year and get it back ususally 3 weeks from filing.

I wouldn't recommend this, but if you overpay for the current year you will eventually get a refund. I accidentally sent a payment in May 2017, intending it to be for tax year 2016, but IRS thought it was for 2016. In November they refunded the money to me (with interest!).

Anyone know the current interest rate for The Bank of the IRS? Is it better than the paltry interest you can get from most brick and mortar banks, the Internet banks or short-term government paper?

Hoping to clarify this strategy. If I make a tax payment in the amount of X on pay1040.com, and I complete my taxes and am found to be due a refund anyway, but the refund is calculated only as the amount I overpaid in taxes (not including the tax payment I've made on pay1040.com), how do I get it to also add in the amount I've submitted as tax payments to refund me along with my normal refund?

The refund will include your pay1040.com payment as long as you included that on your tax return...and you would definitely want to include it!