If you don’t like rants, don’t read this. 
This really seems more complicated than it needs to be. I understand that envelopes are not restricted to just one of my accounts. What I don’t understand is why I have to transfer from unallocated envelope to a ‘cash’ envelope, then from my checking account to a ‘cash’ account, then a payment/transaction to get the actual withdrawal amount, and then another transaction to pay a debt using part of the cash. Surely there is a better way. All I did was take out $40 at the ATM & give my inlaws $20 cash for a partial bill, which is a debt transaction that requires having a separate cash account.
Cash is just an example. I have several Savings accounts that I am trying to add to bit by bit. It’s the same thing. An envelope transfer, then an account transfer, then perhaps I need to pay a bill or take out cash & I need an envelope or another account for each of those. If I need an envelope for each account, why upgrade GB? It’s less confusing to just use envelopes.
Perhaps GB should have a separate group of envelopes for each account, rather than a ‘total’ group of envelopes that show everything. Or allow it as an option. If I’m transferring from one bank account to another, it’s simpler to literally just transfer from one to the other and manage them individually as needed. I have messed this up so many times in the past month because if I forget ONE of those three transactions, I am screwed. I’ve had to go back in and correct ‘current’ account balances several times just today because I’m trying to figure out which transfer is missing or misallocated.
This was honestly easier before I upgraded to track all of my accounts.
I think I’ll need to wipe everything and start fresh July 1 just because my eyes are going buggy trying to see which transaction is associated with which.
Given how little money I have to work with, spending a whole day trying to clean this up doesn’t seem worth it.
Also, I started trying to sort this out when I was coming down with Covid, so that didn’t help my confusion.
Am I missing some kind of easy approach to this that is obvious to other people? It wouldn’t be the first time. 
I’m confused. Are you tracking your in-laws’ debt? Or are you saying the $40 cash from the ATM came from a credit card?
Every time value moves from one state to another you need a transaction. Converting from bank account to cash or from CC to cash is an Account Transfer. Giving that cash to someone else is an Expense. Prefilling or backfilling an envelope is another transaction. So, yes, if you have an ad-hoc expense that you didn’t budget for ahead of time, you could very easily need two or three transactions in GB to accurately capture what you did.
When you gave the $20 cash to your in-laws, it didn’t have to come from a ‘cash’ envelope. It could have come from any envelope. I can think of a few cases where an account-specific envelope is useful, but ‘cash’ is not one of them.
You don’t need an envelope for each account. Unless you want to. I have one Savings Account and a dozen or more Savings Envelopes. The envelopes allocate my savings among various goals and funds, but there’s no reason to physically move the money into separate accounts at the bank. Maybe you have reasons to do that, in which case you’ll have to do the extra setup and transactions in GB. Maybe you just have too many accounts.
In general, you should have a small number of regular Fills per month. I fill once on the first day of the month. Others fill on their paydays. I pay for 95% of transactions using my debit card so the vast majority of my expenses require only one entry in GB.
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If you’re tracking your cash (and it sounds like you are) then yes, you’ll need a “cash” account. If not, just enter ATM withdrawals as money spent and call it a day. Likewise, your payment to your in-laws could be a $20 transaction from your bank account; it doesn’t matter if you took out cash and gave it to them or if you used a debit card or even wrote a check.
Since I DON’T track my cash, in my ledger that would look like:
$20 Misc/Cash spent from Bank A, and
$20 Debt to In-Laws from Bank A. In the notes I might say it was a $40 ATM if I think I’ll forget when it’s time to reconcile, but the transaction is the same.
I owe them money. I’m tracking the debt.
I had seen a suggestion here to create a separate ‘cash’ account and it seemed logical as a way to compile cash withdrawal info when multiple accounts might be involved.
I have more than one account & I want to track them all. But perhaps you’re right. It certainly was easier to not have multiple accounts - or to ignore them.
I do keep a cash account, I just don’t track my spend there. And maybe it would be easier to put all your savings in one envelope? Unless you’re saving for different, specific goals?
It does sound like you’re doing a lot of extra work but depending on how granular you want to be, that much detail can be helpful—but not if it’s too much to actually keep up!
Maybe you’re right that it could be one envelope.
The debt account must have an envelope associated with it, right? It’s been ages since I tracked a debt in GB but I think that’s how it worked. So you withdraw cash at an ATM, that’s an Account Transfer from Checking to Cash, you Fill the Debt Payment envelope from Unallocated, then you make the debt payment transaction from that envelope using the Cash account. It is three separate money movements so three entries in your ledger. Anything beyond that, such as moving it through a Cash envelope, is just extra steps.