That could be your dad or anyone else, but family will usually be your first choice.

Rather, I think this is more about discretionary investment income that you have the choice whether to just let sit in a savings account earning next to nothing so that you don't miss an opportunity when it presents itself. 

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.