Well I use Console, not Rest (different trust accounting software) (our ledgers are much easier to read), but It's pretty simple.
The third and fourth columns in from the right are the paid dates. ie - the last payment of $440 paid the tenants from the 14/9/12 to 27/9/12 (two weeks).
The amount "in hand" appears to be rent in credit, which makes sense. The "in hand" amount is collected as rent but isn't included in the dates, as it's not a full week's rent of $220.
The last payment was 27/9 as you pointed out, however this payment was made when the tenant was 10 days in arrears. Naughty tenants.