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. 

Plumbing by-passes or abandoned lines; collapsing sewer lines; badly corroded supply and waste lines (both can be from inside or outside corrosion) fixtures with very hard to find components; hidden electrical junction boxes...or non-existent boxes at junctions; outdated and/or underrated distribution panels; knob and tube wiring improperly connected to, or extended with, romex; Switches wired incorrectly, breaking the neutral instead of the hot side; no, or poor grounds for improper outlets; overheated connections, outlets, switches, and light fixtures; improper wire sizes for circuits and overloaded circuits; and plenty of others...all very costly to troubleshoot, locate, and correct individually.

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 and your Dad can get involved if there are major unit turns or CapEx decisions, but let the management company lease, handle maintenance, landscaping, etc.

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. 

Depending on the size of the yard the landscaping clean up is usually cheap.

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

Contracted out most work and put in a little of my own sweat equity in the kitchen and landscaping.