What are your needs??
When do you need a place?
How many people are going to live there?
How many children? Ages of Children?
How many bed rooms and baths are you looking for?
How many cars do you have?
Any pets? Any cats?
Do you have first months rent? Security deposit (typically 1 months rent)? Agents fee (typically 1/2 to a full months rent)?
How long do you plan on being there?
Single family home rentals may require you to pay for heat, electric, water, lawn and snow maintenance.
Are you working?
How is your credit rating? Will you be able to get references?
Hope this give you some idea of what answers you will need to have in this competitive rental market.
Other great schools systems - Brookline, Newton, Needham, Dover, Wellesley and Weston to name a few.