@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.  

For six months, I’ve been working a sales job in San Francisco which pays well for my age (~80k/year), and am extremely fortunate to be able to live at home with my parents in Berkeley and save on rent.

I can't decide whether this is an indication of a positive trend of more people understanding the value of real estate investing, whether we're just getting to an age where a lot of people are starting to consider retirement planning, or if it is an indication of the "every man and his dog" mentality and a sign of irrational exuberance?

ask him at what age does he want to retire, or is he the work til he drops type of guy.2. trying to pay for, rehab & manage/maintain properties as a husband & wife team is exponentially more difficult when you have little ones running around.