Yes, stroller swaps are a great idea and they work. I participated in one and it was great to not have to take a stroller down with me. Look around and find one that fits your dates and needs, then sign up.
Just remember. Stay in contact with the persons before and after you and let them know immediately of any changes in your plans.
When you leave, if you can't hand off the stroller to the next person, take the time to take it to their resort and leave it with baggage services and get a claim number. The stroller on my swap was lost when a participant ask baggage services to do a resort transfer and didn't get a claim number.