I fear there may be a misunderstanding here of the process Krogoth and I are advocating. It is not my place to tell anyone what to do or not to do; nor what anyone's risk tolerance ought to be. And I'm going to risk sounding patronising here by getting a bit preachy in the hope you and / or others who see this don't jump into doing this stuff, get it wrong and get robbed.
But above in this thread (here...
Securely Withdraw a Bitcoin Paper Wallet: Offline Signing with your air-gapped Phone via Electrum
... as well as in this post: https://bitcointalksearch.org/topic/m.55893024 )
...and, I suspect, in countless other threads and videos and books about the basics of Bitcoin, there are processes devised, tried and tested to handle and to use private keys securely. If dealing with anything more than what to you is 'loose change', I highly recommend not only following these processes but also taking the time and effort beforehand to understand what a transaction consists of; what is required to prepare a transaction, how most of the process can be separated from the vulnerable bit (i.e. its signing). Because once it is understood, you will be able to see why what may initially be a daunting many-step processes is necessary; you can follow the purpose of each step and where it belongs in the process; you can get a better appreciation of the design of Bitcoin and the transaction-creating process. And when it's safely done, when you did it, you can get the satisfaction not only of knowing that the funds are safe but also from knowing that, by following an understood step-by-step that you will have consolidated that knowledge by carrying it out yourself. And, as remote a chance as there may have been (see below) that the online machines were compromised, you will know that it was all done without there being a need for a 'hold-your-breath-and-hope' moment when there was a risk of losing the coins*. (The process of using a hardware wallet will also make more sense to you if you hadn't already gotten what that process consists of.)
/soap box rant
The use of Electrum (for the on-line machine) with respect to moving the balance from the physical coin is as a 'watch only' wallet whereby when setting it up, instead of inputting private keys (as you would to restore a low-value wallet with some funds on), you input only the bitcoin address (the part that was visible prior to peeling the sticker off). This enables that wallet, once you've put in the destination address, to find the balance on the blockchain and figure out how much 'max' is in order to create the transaction that you'll be signing on the air-gapped wallet. But I think we're going round in circles by now. I don't think I have any more to add on this process that hasn't already been said or isn't in the resources Krogoth kindly linked to.
The risk is simply that malware on a connected machine could potentially use your private key to move your BTC to their address quicker than your sweeping process does.
You're now asking to quantify risk which is a whole other ballgame. The odds that this could happen vary enormously with each circumstance and would be very difficult, even for a security expert, to ascertain without knowing what devices / OS you're using, what else they're used for and since when, whether you use the same device (or accounts also associated with that device) to send communications relating to cryptocurrency, how good your opsec is etc. etc. Without knowing how big an 'I own crypto' bullseye sign you've digitally drawn on your back, it's impossible to tell what the odds are. But why take that risk if you have an opportunity both to carry out this process without taking that risk and in the process, to progress your learning of what this technology is about?
iBHK8
All good. At least this convo is keeping the thread alive while we're waiting for these photos
*You may even find the process so satisfying that you want to go through it again using Electron Cash for BCH, Electrum SV for BSV before using the simple one-step process in Ballet or Coinomi for anything else.
Wow...okay let me first start off by thanking you and Krogoth for such detail. I honestly thought I had it all worked out prior to this and had spent quite a bit of time on this a while back just to try and learn how to construct a transaction, then be able to sweep or get the BTC off of it first then go back and retrieve any forks or airdropped coins that may be on that private key. However after reading this and letting it sink in more and more the more I'm realizing I have to do much more work here and I have to absolutely learn to be more secure because you're both 100% correct in the thinking of yeah sure you might be fine doing it the way I had learned so far but why take the risk if I don't have to and I can do it SO MUCH more securely. So thank you to the both of you and again good luck with your sale. No worries on the pics. The suspense is building plus I have some learning to do! Cheers and Happy Holidays to all!
iBHK8