AFAIK, the only possibility  here is that you somehow created a BIP39 seed with a different derivation path than the one you are using now.

So, back to derivation paths.
I would try everything if they were my coins.
 Personally, I prefer to use iancoleman BIP39 than electrum...

First of all, remove all  funds that you can from that wallet. Consider that seed exposed and do not use it ever again.


Go to https://iancoleman.io/bip39/ in your tails ultra secure computer in offline mode, insert your seed there. See how it works.
 It will generate all possible addresses on the bottom of the page. If you find your address there, just copy paste its private key to electrum and you are done.

However, do not search for your address there only using the default derivation path, as you know it won't work. You need to try different derivation paths.

Go to derivation path.
You can try the change addresses. Your transaction generated some Change of a few cents....  your coins may be in a change address. 
Set "Internal/External" to 1, so you can see the change addresses. Your address may be there.


Edit:
This 1AoG3kEHzXNfZft5xCmaH1T2UtWjsVvj5c was supposed to be the change address of your first transaction.
Can you find it in tails or in your windows electrum wallet using ismine(1AoG3kEHzXNfZft5xCmaH1T2UtWjsVvj5c )? you didn't use that address again.
This may be important. If you sent a small value of 0.00004438 to the tails wallet, and the big value as a change may have came back to your windows wallet.
Maybe your address 1LP6LQ726YJR9wkPLnHWJEfH335DDuiNtL is a change address of your original windows wallet, which sent the btc.

There may be a chance that your 2k USD never left your first wallet, in windows.
use ismine(1AoG3kEHzXNfZft5xCmaH1T2UtWjsVvj5c ) and ismine(1LP6LQ726YJR9wkPLnHWJEfH335DDuiNtL) in windows.