Besides the fact that selling a smaller contract in the future is beneficial what are the other reasons for splitting a contract? Can points be transferred from each account for that 11 month booking window.
No, you cannot transfer from individual add on contracts. The rule is one transfer in or out per master contract.
The benefits I'm aware of all come on the tail end.
Splitting may net you a greater price and quicker sale if you ever need to do that.
Splitting allows you to will the contracts to more than one person.
Splitting allows you to adjust your point total easily. If for example you find you seem to have 50 pts more than you really need you may then sell one of your small contracts rather than having to keep a single large one, or rather than sell the large one and purchase a smaller one.
Besides the fact that selling a smaller contract in the future is beneficial what are the other reasons for splitting a contract? Can points be transferred from each account for that 11 month booking window.
You can do add-ons to your master contract that would not be involved with transfer issues. If you have separate master contracts - different UY, bought as a resale and not added to the main contract - then you must transfer between them to use the points.