Just some notes on your notes, haha
1 & 2, absolutely right. If you know you're going, if you know no one in your party's going to back out, and you can pay in advance, you're golden.
3: the OP's going in January so, you know, it's "only" 7 months in advance in this instance.
4: The OP's made a few posts on this topic and I missed it previously, but she's booking a party of 5, so unless she gets 2 rooms or a suite (which negates "sleep cheap"), a Value is out. Only a handful of resorts have single rooms that will accommodate 5.
But even if we were talking about a party of 4 adults, renting DVC could be at least comparable to a Value. I can't look up rates for January yet, but the first full week in December, Pop for 4 adults is $1060 (once tax is included). The same week in a Standard View at Boardwalk on rented points (one of the DVC studios that sleeps 5, BTW) is $1140, total. So an extra $16 per person gets you in a deluxe resort, walking distance to 2 f the 4 parks as well as 3 other resorts & the Boardwalk District itself, with all the amenities/restaurants/lounges 5 women of legal age might enjoy, versus a Value resort with some coolish pools with pool bars and a food court.
(Factor back in the fact that it's really a party of 5 adults, then you have to forget Pop and move up to at least Port Orleans Riverside, which would run nearly 2 grand for the same week.)
Now, these are "rack rates" and I'm sure you could get a better deal on travelocity or elsewhere online. And WDW might have worthwhile package deals in January like free dining. But being in a deluxe for $228 per person for the week, $32-ish per night, is not a bad deal.