Using a simple annualized return calculation is an easy way to measure a simple $/in and $/out type of investment, but it fails when the cash flows get more complicated than that. 

. * I like to consider IRR, the measurement that takes time value of money into account.

With 4 other roommates, the more sound proofing measures you can take the better experience it will be.

The lease says: LL at sole discretion will take pest control measures for up to 60 days.

When a pipe bursts, it's up to you limit the damage and find contractors who can fix it in a timely measure.

I normally wouldn’t bring this up because most people aren’t very handy these days, but desperate times call for desperate measures, and being 25 you’re probably my nimble enough to work on a roof.

Sorry for not measurements on 2nd level.

It was pretty frustrating to start out as a Newbie Investor as I  got lots of opinions and comments on what to do at a high level, however, nothing actionable and measurable. 

I always tell people to measure Failure. 

Hopefully prior to the start of the year you had put in some goals that you can measure to track your progress.