Exterior landscaping and hardscaping but mostly just better maintenance and reduced expenses (negotiating vendor contracts and just being more responsive so that little issues don't become big ones).

Many sectors of the city are up-and-coming and there are tons of colleges/universities, major medical hospitals, some professional sports, and factories around. 

Having a clear vision of what you want real estate to do for you will reduce or even eliminate your anxiety. 

Maybe try reducing the HELOC. 

My biggest cost would likely be medical insurance, food being the second, quarterly tax payments, normal bills for the home.Is anyone here living off their rental properties?

You can use that "loss" to reduce the tax bill on other income from W-2 or rents, up to a certain amount in any given year.Paper loss?

My day job is at the anschutz medical campus so ideally, the location wouldn't require me to commute longer than 40min each direction.Thank you!

If you had an apartment building designed for student rentals, I may change my mind, as on a macro level it could bring in better students which may reduce maintenance/damage/issues.

The BRRRR method is designed to help investors limit/reduce their out of pocket expense. 

If it's sitting in a business account can colleges look at that money as accessible cash a college might see as accessible money which in turn would reduce college grant money allowed.