PEP process in SF TimeOff before the bookable end date

[vpathangi]

For a customer we have a leave type with Quota called Annual Leave. Employee will be entitled to get every year 32 days of quota annually.

Now customer has requested the below things for Annual leave.

1.  Employee should be able to apply the leave till Feb end next year - Which is Possible in SF by setting the bookable period to till Feb end.
2.  Employee should be able to apply leave for next year Jan and Feb by Dec 31st of present year from present existing quota – Tried to control via Business Rule, but none of them worked.
3.  After point 1 and 2 PEP needs to be executed on 1st Jan of next year to post 10 and below left out balances to new Time Account(year) bucket. - PEP cannot be executed before as bookable period in point 1 is till Feb end of next year nor interim rule can be used to run as there will be future dated leaves in Jan and Feb.

Can you provide the solution/options for Point 2 and 3.