The gentleman has a property in a very small town in Western MA (about 1 hour 20 minutes away from me).

I'd watch your maintenance costs as well on an older property, and be sure to include snow removal in your planning. 

Do we invest in a 3-4 unit older home with good rental history but probably needs quite a bit of maintenance (and might not attract the best quality tenants at the rental price point) or do we go with a newer duplex that is basically turn-key but doesn't have a rental history because both sides were owner-occupied?

There is some high end activity but i am interested in some multfamily for seasonal rentals.

Life always seems to revolve around houses.I have been interested in real estate for a long time, seeing a great aunt rent the house next door and talk about how the rent check covered the mortgage on the house and part of the taxes on her next door house, which I though was incredible especially as I grew older and learned about the tax benefits of owning a house and rental house.  

The real pros like yourself and this Bp gentleman below are the kind of folks we need to pay attention to make it now.

They may require thousands each to make livable.Check the age too for moving them they look older and a lot of transport companies won't move older homes because its not safe

However, I read stories on how older investors act as mentors to newbies and give them incredible deals on properties. 

hi gary. i would be happy to meet with you. i live in bufflo, ny, however. lol. i do get to grand rapids often, but i do not have any plans to be there until hunting season in november this year. my brother does still live in the grand rapids area. i am sure he would like to meet with you as well. i will let you know when i will be in town. see ya then

You're a gentleman and a scholar.