You can use Pinside to help find Pinside members that live near you, and since you live in a major metropolitan area there should be quite a few. Click on Community at the top of the page, then on Pinsiders, then use the map to help find them. Reach out to a few members near you and you may find one that will help service any pinball machine you buy, and of course the forums here on Pinside are a great place to obtain advice when something on your machine needs to be serviced. Those Pinside members near you may also have machines of their own, and frequently they will welcome someone to come and visit them to play their machines - you may find something your family enjoys playing that way to help you know what to look for. An experienced Pinsider could also help you in using the Pinside Marketplace to help find machines being offered for sale by Pinsiders.

I'd strongly recommend buying your first pin locally so you can see and play it before taking it home.