"What should I look out for or be wary of? " - Make sure during C19 you read and understand the cancellation policy.
""The Shire." Has anyone heard of it or seen it? " - I haven't heard of that community.
I'm just wondering if you have considered condo resorts? We were going to rent a house at first when we traveled with extended family but when we looked into WBC we were sold. They offer a house feel with resort amenities. I would recommend Wyndham Bonnet Creek. They have 1, 2, 3 and 4 bdrm condos plus numerous pools. They are close to Disney, so uber/lyft could be used if we wanted to split up. Disney Springs is close just in case you don't want to cook plus numerous other restaurants and a
Walmart down the street. They also have a few onsite restaurants. The resort is clean, updated and the condos are very spacious. You will feel like you are in a house. You will definitely be able to spread out if you are a family.
We have visited with 10 and 3 persons. Our family trip with 10 persons was 3 grandparents, 4 sisters and 3 kids. We stayed in a 4 bdrm condo and it was more than enough room. Every family had their own room and bathroom. My sis#2, sis#3 and niece(6) shared a room. It had two queen beds which they loved. We stayed a week and after a few days you know how you need your space from your siblings/family this condo did the trick. On our chill days we were not on top of each other and we were able to relax.
When my DH, MIL and myself went we rented a 2 bdrm. My MIL was so excited that she basically had her own half of the condo. She couldn't believe how spacious it was. We stayed a week and she enjoyed herself tremendously. She goes to bed at 8pm and wakes up with the chickens. She would read and peruse the resort until we woke up and started moving around. She didn't disturb us and we didn't disturb her when we stayed up late.
Anyways, just thought I would give you another option. I was overwhelmed by all the homes available so I know what you are going through. We're headed back for another family trip in 2022. Two sisters have since gotten married so we'll probably rent two 3 bdrms this time. We thought again about renting a large 6-8 bdrm home but decided against it since WBC is so close to WDW and we know what to expect from WBC.
Good luck with your search.