I have my first offer for SSR being ROFR at the moment and I'm happy with the price, points, etc ($92p loaded but sellers paying 2024 dues which I equated to $8/p bring me to $84/p.. don't pop my bubble if you see it differently please) but now I'm thinking of a possible second contract.
My husband and I had different views on which contract end date to pick so we ended up in the middle. I wanted CC because of the longer contract and he wanted OKW so we weren't committed for a longer period of time. We split the difference and ended up at SSR.
I'm a value resort girl but the kid is getting older and will probably settle down as she graduates grad school later this fall. That means grandkids and a larger room so
DVC made sense to me (still had to convince him). We don't plan 11 months out.. very rarely plan 7 months out so I realize I'm most likely getting SSR and OKW. I'm 100% OK with that.
That said.. I'm looking at a possible second contract later in the year to add additional points and started doing a bit more research, reading the boards more, etc. and have a ton of questions. Feel free to answer as many or few as you would like

I'd love to be educated!
On the "forless" site they give the deal "stars" and you can have very similar points, available points, and price per point but one is rated two stars while another is 4 stars. Other than UY, what else would drive the deal rating up?
I can't get over the price swing between resorts. If you take CC and review the current contracts for sale there is a $78 per point difference from highest to lowest. I know the number of points and if it is stripped or not make a difference but that is a huge swing.
Knowing we are good with SSR and OKW and we don't plan vacations very far out (I'm looking at 4th of July flights tonight) what am I missing by only considering SSR for additional points?
If I buy a 2nd contract with a different UY, as long as the points are loaded can I use them for a single booking?
Of the places that site aggregates into the single view - I'm assuming they are all tried and true brokers and the risk of being scammed is low? I messaged one a couple times because a contract I was interested in had different available points on their home screen vs when you clicked into the details. That was about 3 weeks ago and I still haven't heard back.
Some of these contracts have been on the site for LONG periods of time. In fact, one is 878 days as of today. Do you think these are valid contracts? Are the sellers firm on price or do you think they may have been firm on the price and now they are so old they don't get looked at? What would prevent them from relisting to get fresh eyes on them?
When you make an offer on a contract, what is your thought process? How are you making the decision on what to offer? It is the people pleaser in me that doesn't want to low-ball a seller. How do you get over that feeling? Again, I'm happy with my offer but I also in the back of my mind keep thinking what if I offered less since they accepted my first offer.