Both are possible with a little bit of rule trickery.
For the DD-MMM-YYYY scenario you would have to create 12 rules (1 for each
month of the year) on the date picker to set the expression box's value, as
well as a condition on each rule to run only when the corresponding month is
selected.
Example rule for February:
Action: Set a field's value
Field: <your expression box>
Value: concat(substring(., 9, 2), "-Feb-", substring(., 1, 4))
Condition on rule (Select "The expression" from the first dropdown list box
in the Condition dialog box to be able to enter the following expression):
number(substring(., 6, 2)) = 2
For the DD-MM-YY scenario you only need to create 1 rule on the date picker.
Action: Set a field's value
Field: <your expression box>
Value: concat(substring(., 9, 2), "-", substring(., 6, 2), "-", substring(.,
3, 2))