@Ryan Murdock - I have a few century old rentals too, but they are my least favorite for buy and hold.  

A century of weekend warrior home improvements can lead to lots of expensive surprises, however, if you (or your inspector) are able to accurately assess what to expect it's just a function of crunching repair numbers.

I thank century 21 the owner david c howard for helping me along the way also thell woods . these guys are the true gurus of the game ..helped me alot along the way. thanks to biggerpockets aready helpin me out too.. give me a shout anybody anytime!! 

Mentors for almost any profession, have been accepted as very good things for centuries...and yes, there are always the ones you wouldn't recomend.  

Older homes should have windows appropriate to their own period, not 21st Century looks.If buying a home for yourself, go for it!

The buyer wants a deal and makes their calculations based on getting the deal of a century. 

But, it will cost a lot to get it from it's present condition to a 21st Century B to B- condition and desirability. 

If one of the 10 greatest investors of the last century doesnt think they can predict a correction, why do all of us then think we are Nostradamus?

Go to a local brokerage (Century 21) and talk to a few agents about your idea.One will like it and tell you where their meetings are held each week.

Building surrounded by a Century 21 office, Restaurant/bar, and large hospital.