Michael, something I want to add to your spot-on comments; I see a lot of inexperienced STR buyers, buying a property to be a STR either on their own (FSBO or through the listing agent), or through a buyer agent that has little to no experience with STR's and who doesn't have a a great STR network, strategy, has no ability to analyze a property's STR potential, doesn't know how to assess and recommend remodel or what it will cost or how long it will take and what's required by city/county, etc.

Some cities have no problem putting landlords in a bad spot should a tenannt not pay the process of eviction in your area I don't believe is short.

I spend my winters in Colorado and want a get away spot I can go on weekends to relax be close to nature.

Say you're checking out a couple of spots, one's 1,000 sqft for $1,000 a month, and the other's 1,200 sqft for $1,300. 

They'll make sure your spot stays super clean and everyone stays happy.

It doesn't take long to learn how to spot a good deal.6.

The lots are small and there is no way I can get a spot for each unit on the property, even at four units this is next to impossible.

I'm also 40 and spent a lot of my 20s and early 30s doing nothing but working to get to this point. think you are spot on here

Keep the cute house neat inside and out.Annoy thing: since she moved in, she asked to replace dryer, then dish washer(said after washing will have water spot on dishes), then clogged under kitchen sink after Thanksgiving, add light... finally we had a quite holiday.   

As far as a multi, personally if all things were equal I'd go for the multi for a few reasons.  1) Added diversification.. if one tenant doesn't pay, you can still cover property expenses with the other tenants 2) Shared capex... typically, one roof and one property to maintain but multiple streams of income 3) Less vacancy.. usually multi's rent for lower, for example one of mine is the sweet spot of 3 bedrooms for $1300.