The longer a tenant stays, the more likely that they will get more of their security deposit back because things naturally age and need to be updated over time and we can't charge tenants for "normal wear and tear."

@Trevor ScheidererCondition and age of the property will be a large part of determining a sufficient amount to be expensed for capital improvements/repairs.

And in the suburbs it can be useful when comparing property in the same development.Otherwise, you have to take into consideration the variables of lot size, garage or no, age of home and recent reno or no.

@Charlie Van Norman I don't do student housing but it does sound like an excellent idea as long as you are in the age range of the students. 

My question is can I make this work to MY advantage at my age?

This is a great benefit since you are able to access your retirement funds at an earlier age.

My main concerns is the unknown age of the roof (10+ years), original windows (roughly 12 total), and the 5 young children that will be living in the house. 

I dont have a lot invested in my 401 and given my age not enough to retire from.

I really wish I had know what I know now at your age, I would have loved to have started earlier and begun that compounding process at an earlier age (which makes a huge difference in long-term wealth building).

Any time you work on a 2 story home of that age especially there are a lot of load bearing walls.