You're going to have to move both up, albeit property taxes in CO aren't bad but insurance needs to be fit for a house hack if you're going to have a bunch of tenants messing stuff up. 5% maintenance for a 5-member house hack is rather light. 

It simply depends on how much time, energy, and commitment you have to invest.

I'm reaching out to see if anyone can recommend any general contractors that have experience/expertise in light rehabs for converting units into Airbnb properties.

You can go after them in small claims court, don't waste the energy. 

Cosmetic upgrades including new appliances, vanities, lighting, flooring.

Property is a triplex, on the river, 150 of water frontage, lots of light maybe thinking renting long term one, and airbnb the others. 

No, their eyes dart between the clock and the road, long practice assuring them that if they make it to the second light on Maple by 8:22 they still have a change to pull into their job's parking lot by 8:39 and punch in before their 8:45 flex-time deadline passes.

I make sure that the roofs are in good condition, the siding, replace windows if they are not energy-efficient, etc.

I think we could probably get $500+ with a light rehab.

Check to see if you have to install any manholes, fire hydrants, curb, gutter, sidewalks, street signs, street lighting any specific street design or access requirements, Check DOT requirements for access, stop lights and permits, traffic studies, DWQ requirements for permits, permit fees and time frames.Once you have an idea of what you can build and what is required in terms of permitting and infrastructure you want to talk to some civil engineers and commercial general contractors that do the type of projects and build the type of buildings you want to build so you can get an idea of costs, time frame and requirements.