I'm sure this information is somewhere in these very helpful boards, but I was having trouble finding it on search. (This is the point where all experienced Disers are entitled to one eyeroll at my expense!

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It is my first time renting a condo/townhome. I have sent an request with my dates to Windsor Hills and received a number of responses from owners. I am beginning to narrow down my choices.
Is there a checklist of questions I should be asking to help me decide?
Thanks.
Well it's mostly going to come down to what you're looking for in a home.
Amenities like:
internet
premium mattresses / beds / linens
TVs
Electronics / TVs
Video games for the kids
pool / no pool?
free phone calls
who is their MC? Do they have a local MC...and are they good?
quality of the home / furnishings?
Pictures of the home?
Price?
There IS variation from home-home in terms of quality, and you also tend to get what you pay for. The question is...what's important to you? What are you looking for in a vacation home? My DW is very picky about the decorating for instance, and wouldn't stay in a basic / low end furnished home. Amenities like awesome mattresses matter to us as well, we love to sleep in a super comfy bed! (We went on a ski vacation over New Year's and had the exact opposite, just awful when you're tired after skiing all day!).
Some on the DIS will tell you they found what looked to be an absolute bargain (not necessarily in WHR), but the home was not as well equipped as they would have liked when they arrived. Just something to consider.
Wish I could give you more criteria than that, but it's very much an individual decision. I can tell you I've been in dozens and dozens of townhomes in WHR and homes as well (with realtors, looking to buy), and there's some that I would consider to have premium furniture and amenities, and some are much more basic. I would be looking for a premium place personally, the price difference isn't all that much, if we were to buy another place (we're considering it) and it had basic furniture, we would rip it all out and start over, but that's just us!
A pool is also very important to us, we use our own private pool more than the clubhouse, it's just so convenient, the kids can swim any time they like without us having to all traipse over to the clubhouse. Location isn't as much of a factor for us...if we're 1/2 block or 2 blocks to the clubhouse...same difference..we still have to move ourselves over there, as opposed to going in the back yard.