I use separate accounts for every multi-step transaction like a cheque
which separately issues and clears.  I enter one transaction when I
issue the cheque; then a script converts a CSV bank statement into a
transaction that clears the cheque.  For example:

; hand-written ledger entry
account Liabilities:Bank:Cheque:123
2017-01-31 Landlord
    Expenses:Rent                            $750.00
    Liabilities:Bank:Cheque:123

; automatically generated by bank2ledger script
2017-02-25 Bank statement          
    Liabilities:Bank:Cheque:123              $750.00
    Assets:Bank

Here's a more detailed description of how it works:

https://mumble.net/~campbell/2017/02/26/ledger/HOWTO-reconcile-cheques

I do the same for other transactions than cheques too.  The only
hand-editing occurs when I don't have any kind of transaction id
number printed on the receipt, or when something is amiss -- more
details here:

https://mumble.net/~campbell/2017/02/26/ledger/HOWTO-reconcile-payments

I also put the date in the account names these days so it's easy to
march through pending transactions chronologically and figure out
what's up with them using just `ledger balance pending'.

I also use a similar idea to track outstanding orders, so that `ledger
balance orders' will show all orders I made that have not been shipped
or otherwise fulfilled: enter a receipt when I make an order as one
transaction with a date and order number in the account name, and then
enter the packing list as another transaction clearing the order.

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