We will be back at WP for the 4th time on Oct 29, so that says a lot. We have also stayed at Windsor Hills. WH is a few years newer and the pool has zero entry side and very plain, small waterslide. Compared to newer resort facilities with waterfalls and slides, etc, both are pretty dated, but still enjoyable. WH pool is very leisure-oriented where you could swim some laps in the WP pool, if so inclined.
The difference in distance between the resorts and WDW is really negligible, particularly if you take Entry Point Rd. Aka the back road. While we like the thrill of driving under the iconic Welcome sign at least on Day 1, it is a treat to avoid the traffic and sometimes confusing signs on the main roads leaving WDW. We just follow the signs for the AKL, and there is a turnoff between AK and AKL that leads you straight out to 192, and a few min later you are at either of these resorts. Often feels like the red light is longer than the Drive!