Question for you, Sandisw. What do you find yourself valuing more when getting a new resale contract, price/pt or UY? From everything I have read it seems managing two contracts with different UYs is harder than if those contracts have the same UY. Totally understandable. But if you found a contract you liked, yet the UY was different than your one other contract, would you hesitate to get it? I guess what I am trying to gauge is just how difficult it is to manage different UYs. Is it so difficult to keep you from pulling the trigger on a contract you liked?
It really depends on the size of the contract. If you can manage the new UY by treating each one on its own and not worry about transferring, or okay booking some nights of a trip on each one , the different UY can make it nice. That is how we ended up with Aug UY points because I just couldn't pass up the 300 point SSR contract at $73/point in 2017.
Now, other than a very rare time when I did the transfer...was selling so I needed to..I use each one on its own as though that is all I have. Currently, my Dec UY has SSR and RIV resale and my Aug UY has SSR and RIV direct. I will add VGF to the Dec UY.
Because of the way I have things, I don't worry about borrowing SSR points in one UY, even when I may have some in the other because it keeps it clean. IMO, if you treat things like this, it really is doable.
If I was going to go with a second UY, I would try to make it so that you hedge your bets to cover all the month...for example, I wouldn't get a Feb UY if I had March....but might get a Feb UY if I had Sept since it puts them far enough apart.
One UY is going to be easier in the sense that you can just book your trips without ever having to think about which contract to use or where the points might come from at 7 months if different resorts or 11 months if they are the same.
But, ultimately, price and size of contract would always win for me. I don't find it that hard because I don't combine. My Aug UY points cover my fall through March trips and my Dec UY points cover Dec through July trips. As I have shared, some trips during the winter months use points from both and that is when I have linked the reservations!
ETA: I more often than not do split stay so that has made it even easier for me because then it doesn't matter.