Two deeds recorded means two taxable transfers in most places, so yes, plan on paying it twice. There's no rule that a fast resale counts as one event. The deed from the seller to you is one conveyance and the deed from you to your buyer is another, and each gets looked at on its own.
The size of that varies a lot by state and sometimes by county or city, so the only real answer is the one your local title or escrow officer gives you for that specific address. Some states have no transfer tax at all, some charge a small flat rate per thousand, and a few cities stack their own on top. Confirm the number in writing before you sign anything, because it comes straight out of your spread.
When people say two sets of closing costs, they usually mean recording fees, escrow or attorney fees, and title work on each side. Transfer tax is normally counted separately, which is why the all-in number surprises people. Who pays it is also customary rather than fixed. In some markets the seller pays, in others the buyer, and in a double close you may end up on the hook on both sides because you're the buyer in closing one and the seller in closing two.
The other thing worth pinning down early is whether your title company will even do back to back closings and how they want the funding to arrive. That answer changes your cost more than the tax does.
