@Michael StewardYou have good vision and your conclusion is correct.

From the vision you have created for yourself, it already tells me that you have been listening to a lot of podcasts and reading a lot on these forums.

Before you strategize, I would sit down and do some serious thinking about your 10 year vision.

But for long term appreciation / wealth growth, I don't have that sort of vision to really say that people will like to hotel-style living. 

It sounds like your passion and vision for the property are indelible so I would encourage you to go for it!  

I have a vision for where I want to be in life in say, 10 or 20 years, however I haven’t found the path to get there yet.Any advice or guidance at all is genuinely greatly appreciated for this newbie as I am settled on making Real Estate my life’s work.

Overall, I worry the demand will weaken for the peripheral markets around Bend if the overall market softens.  

Kudos for having the vision to see what others failed to realize and holding that property. 

Many things must go into the equation to be successful in life, including RE: discipline, hard work, eagerness to learn, dedication, clear vision, being a nice human being, being likable, respectful, honest, and on and on.

There is a lot of older properties with upside potential, often overlooked but with the right vision can be pretty lucrative.My partner and I just closed on a multi-family property in the area and are currently renovating ourselves to bring in higher rents.