From a marketing psychology perspective the great part is you are triggering them to come to that realization you aren't pushing it on them.

20 years ago. second best time is todaySpeculation won't get you anywhere unless you want to take big risks and hope this or that happens.If you have a consistent strategy and hold/manage/rent then in the long run you will do very well.Maybe some short term fluctuation but learn to live with that.There was a psychology experiment where investors where given two funds into invest in.

@Cameron Riley "A crazy tenant" is most often a psychologically battered human being under immense mental stress.

While I undestand the psychological wins associated with paying off a small balance loan, it seems hard to justify paying off a $3000 student loan at 3% interest if you have $10000 in 24% credit card debt.

You'll wonder why you're doing all of that work, but it helps you to spend less time actually painting, and get a better result.Another kind of psychological thing is that it will look worse before it looks better.

Also maybe find econ or bio majors instead of psychology ;)

Psychologically, it's going to weigh heavily.Retrospectively, what would I do if I ever chose to sell the condo?

In my mind, College is the physical and psychological barrier for "quality" real estate assets in the area.

Finance, Marketing, Psychology, Construction Project Management,  Accounting, Business Law, Real estate Principles to name a few. 

You're totally right about what should determine value, but as you know, both buyers and sellers are influenced by psychological factors, including knowledge of what you paid for a property.