The areas that you have mentioned are all very nice, but it depends on what you are looking for. Do you need train access into Boston? Lexington does not have train access, but it is a short drive to one. Weston has a more wooded/rural feel to it, but I don't think there are many rentals there, however, take a look anyway. Weston's town center is minimal whereas the other two towns have a more significant town center. Also, the three areas you have mentioned have all great schools if that's also a concern. I live in one of the towns mentioned so I have a pretty good feel of those three locations. Wellsley is also a beautiful town which you may want to consider, but I think there are only a few rentals there if any. Take a look anyway. They have a commuter rail that goes through there as well. Good luck ! My family and I have been through this as well and we came from California.
There are a few here already.
Winchester and Lexington are next to each other, and Weston is in a different area, so you may need two agents/brokers.
If you are renting for at least a year, why not buy?
You might break even in dollars and still ge the tax advantage of interest deduction.
It depends on what your rental budget is, your tax situation, and what your requirements are, of course.
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While I do not typically cover the areas you mentioned, I can send you some listings to get you going with familiarizing yourself with the inventory. If you see something you like I could assist you in finding a local Realtor to assist you.
Please feel free to reach out if you would like me to facilitate the beginning of this process for you. My contact information can be found in my profile.