The lucky part for you is that there are many fewer people who are in the multi market than the SFR market so it should increase your chances right out of the gate so to speak.Also depends on DOM (days on market), at some point the bank will want to clean up the balance sheet for the month or quarter etc etc and if not sold, will begin dropping the price, sometimes dramatically.

Being that I would like to keep the tenants, I would never make the dramatic jump to market value, but I plan to get there incrementally (perhaps over two years).

It is key to list your property at the appropriate price, as your credibility in the marketplace will dwindle dramatically after the first 30 days and low ball offers will start coming in if any.

As far as the area around Madison I have no idea about it, but if there is some huge developments under way that could push the appreciation aspect up dramatically over the next 10 years or so then maybe if you don't mind losing money on it and living in it just to off set cost of living then go right ahead.

Everything done here is entirely legal and proven.I apologize to all on the forum having to read such dramatic posts, really seems to be counter productive but I guess at the end of the day it's good for questions and issues to be addressed.

The life of the roof can vary dramatically depending on your location, number of trees around the house, weather, pitch, shade/sun exposure, etc so you'll just have to make your best guess at how much life it has left.

It varies dramatically per city, per market and per state...The curve attached shows where cities are in the cycle - very useful!!!

Prior to looking at the history, I came up with $112,500 - dramatically lower yes I know but this is what trails out of my numbers.

@Jay Hinrichs is definitely right about living cheap being a consideration but once you look at taxes and insurance the cost often will go up dramatically.  

Not that dramatic most of the time but down none the less.