We did estes park and Denver this past summer. Denver has a light rail system that may be an option just don't forget to keep track of times on the trains. Uber or lyft is probably better option than cabs. I think their cabs only did airport runs.
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Looked everything up on Expedia and the total with tickets would be $487 for me.
Kinda pricey, but the flight is the majority of it. Still way cheaper than Big Smoke in Vegas
Would only have to not buy anything for 1 month, then only a two thirds regular order max and I would have enough, so definitely doable
I friggin' LOVE cigars
Not ideal travel but you check bus tickets? Takes longer but your not driving