Poor choice of wording on my part.

@Caleb Brown So basically it comes down to how big of a risk I'm willing to take, there is no wise choice. 

You've already been introduced to @Basit Siddiqi who is a good choice to get started with and I can give you CPA names in Scottsdale that do high end investment planning if you want to PM me.

Bend is a beautiful area with 300 days of sunshine (and becoming more popular for tourists and retirees by the day).

If it is a popular vacation spot, then yes it will probably be a vacation rental, but short term could have many different niches.

What kind of leverage you have if any in negotiations will generally depend on the quality of your site for their business type and what alternative choices do they have in the marketplace?

With the crazy rise in cost of housing here, condos are gaining popularity because it's all people can afford and young professionals like them because they tend to be in busier downtown areas.

Your choice is to lose money from this unit, or pay for a better fix. 

Not sure if that is the reason for what you're seeing but then again, Redfin wouldn't be my choice to get that data.

A few popular events: Flipping Mojitos, Gwinnetwork, Atlanta REIA.