Seeing as you are starting out I would not recommend a multi-family yet as it can be more complex to manage & maintain.

Nothing to maintain, agricultural exemption so minimal property taxes, no insurance required, no toilets to fix, no management.

Since most houses were built in the 1900s, the cost of maintaining compared to demolishing and rebuilding is quite low.  

Does anyone have any experience with maintaining the cleanliness of common areas?

Rates are great right now, but I just wouldn’t expect to get the same rate as you have on your house for this one.With Condos the bank has to rely on the HOA to maintain the building, otherwise the property can lose value, and the bank can’t control that.Also, borrowers are more likely to let investments properties go, than they are to let there homes go, in the event of financial hardship.These additional risks factor into your rate.

Why would you accept the risk of renting to someone who won’t live there, with occupants who have no interest in maintaining your property and no financial repercussions?

It’s a middle class play where paying bills and maintaining a life style is important vs building an empire unless of course you use cash flow to reinvest in other assets.

It's in pretty nice shape and with the exception of the in process refinish job on the floor in the livingroom, it has been well maintained and not much needed to get her ready to go. 

It comes fully furnished and maintained...which we both see as needing anywhere from $2500 to $8000 on updating depending on how far we want to go which includes known CapEx.Now this is manaanged, maintained, cleaned and has low taxes, by a local group, Big Powderhorn Lodging Association whom previous owners have been with for over 10 years....anyone have any experience?

She left no will, and our friend is left to maintain the property while it goes through the courts.