I have recently started diving into the idea of house hacking to start my career in real estate so bear with me...I have no actually plan yet as I'm still learning but I'm gonna run down an idea I have in hopes to gain some knowledge. 

Bill market/bear market, that’s a bad strategy for either one

However, many would argue that location has a direct bearing on the ability of an asset to perform.

The one thing I will do to my units to make them more attractive to tenants is I will spend a little bit extra to put in slightly (but not extravagantly) nicer finishes ... things like brushed nickle hardware instead of brass or chrome, laminate floors instead of carpets, etc. and keep my units in good condition ... therefore, even if I charge market rent it is a good deal since my units have slightly nicer finishes ... if I take pride in my units and they are in good locations, then I find it will attract quality tenants who will also take care of my units, and no they do not leave when I raise rents up to the max the market will bear.

One of the attendees, who is also a client, is consistently sharp (Well, actually, most of the attendees were; the average bear does not take time & money to attend such an event.) and asks good questions. 

Does this mean that the good times have come and gone, or that greater discernment and effort need to be brought to bear on the decision-making process?

There is so much "free" info out there where you can get a bearing and learn

Bear in mind they've already returned the money to your former tenant.

. , other factors to consider would be are there major universities nearby?

Its not mailbox money but if you are willing to do the work there are plenty of markets that are under-served (despite the myth that the whole industry is overbuilt: bear in mind that this business is one that markets to a 3-5 mile radius so a market that is overbuilt could be as little as 10-20 miles from a market that is grossly under-served).