Currently I am a senior in college on track to graduate with my Bachelor's degree in Management and Administration; however, I have two years of eligibility to play golf and get any kind of graduate school paid for completely.

I’m going to play therapist here…(I’m not a therapist)I think your real fear is making a bad decision and failing which is normal.

It's also a nice bonus to be in a neighborhood that you may want to continue investing in or live in.

I think the appreciation play is solid over time but proximity is hard to pass up for rental demand.  

Bonus depreciation is being phased out, so we must capitalize while we can.

Key features of Denver’s short-term rental laws, rules, and regulations include:All short-term rentals must have a license.Any short-term rental must be the host’s primary residence.All advertisements must display the host’s business license number.All short-term rental hosts must follow rules related to safety, taxes, zoning, and insurance.Hosts who do not follow the rules could be fined, or could lose their license.It sure seems like you’d be risking your primary home and it’s equity on a speculation play.

But recognize that if your agent is educating you along the way, and helping you to understand the market, even if you find one off market, they brought you value too and played a role in your success.

I figure with rent increases year on year cash flow will increase substantially and this is more of an appreciation play as well 

Simply changing a name does not change the underlying fundamentals of your situation and playing name games doesn't circumvent guidelines. 

That also will play a factor in which route you take.