Ask this Old (Multi-Family) House

[David Coughlin]

Right now, I am in the beginning stages of real estate investment spending a lot of my time educating myself. "House Hacking" is probably my best strategy while searching for my first property. I'm single, financially stable, and I spend half the year working half way across the world. I need a place to live when I'm home, and I also want my money to work for me.

With that said, I live the New England area and I am looking at multi-family homes (Manchester, 'Woo'-ster, Boston, Providence). At least 3 units is preferrable and I have no issues with living in a smaller unit. My big concern is that it seems that all these homes are built anywhere from the late 1800's to early 1900's. Every single on of them is over 100 years old! Some might as well be 200 years old at the end of a 30-year mortgage loan.

With basic research, I know that these houses were built to last, construction was better, maintenance costs are greater, lead paint is bad, etc. But are these houses still appreciating despite their age? How much longer will these houses economically last under good management? How would a 'real' real estate investor appraise this kind of home? How do I look at one of these houses and say "now that's a great deal!" instead of "man, that house is older than my late grandparents!"?

Direction and guidance to help my educational and real estate journey is greatly appreciated for this wannabe gonnabe investor :)