Hello all, trying not to be political tonight =)

A friend of a friend lives in Boston, owns a car that is a stick and wants his wife to learn how to drive (she never had to drive before...both are in their mid-20's...being from the midwest I don't understand this but hey, it is what it is).
So he wants to buy/trade for a newer car with an automatic trans.
I'd just make him force the wife to learn on a stick, but again, this is what it is...

He currently drives a 1998 Nissan Maxima, which has passed inspection but the rust is getting bigger. I guess my questions are:

1) will rust cause you to fail a Mass. vehicle inspection ? what is the criteria ? (ex: in PA if the rust goes all the way through the metal, it fails inspection...)

2) car values in Mass vs. Ohio. - His car in Ohio (rusty '98 maxima w/ 160k) wouldnt fetch more than $500) IF it is inspectable - would this number be any different in Mass. ?

3) Any other good car buying tips for the city-locked folk ? not sure his parking arrangements, he seems to think that his mechanic (lols....) might sell it on consignment, but (to me) that seems unlikely if it wont pass inspection.
His last car payment was $200/mo which he thinks he can swing again - are cars more or less expensive in the big east coast cities than the smaller midwest cities ? (or are they generally the same price ?)

I know that Boston/Mass. house prices are 3x what they are in Ohio. Never looked at cars though.

Thoughts ?

-Midwesterner who had his license at 15.5 years old....

__________________
2009 Kia Sedona
2009 Honda Odyssey EX-L
12006 Jetta Pumpe Duse
(insert Mercedes here)

Husband, Father, sometimes friend =)