Your path will likely get you to where you desire, it will just take a little time. 

After considering some of the variables and running the numbers again, I'm looking at pulling a HELOC on the property as a way to hold on to the current property, but also have flexibility in investing in some other OOS markets.I do think Bend will continue to appreciate and grow as a desirable market so I'd like to hold onto the property (plus it has great cash flow!).

While you can't take forever and a day, because a desirable candidate has choices, deciding too quickly can be disasterous.

Desirable location both locally and regionally.6.  

You are also looking at your desired closing date and determining how much time the appraiser needs and anything else required prior to closing. 

Lack of down payment, lack of entrepreneurial personality, low tolerance for risk, looking for the magic key that fits their desires, just want to learn, sold "Castles in the sky" with a gibberish of disconnected statements that while true in a plethora of instances do not add up to truth in any one instance, fear of failure meaning not able to take a financial loss without going into poverty, never told up front how much money they will need to spend to buy the investment in addition to paying for the class.

While I haven't remodeled the main house, it's situated in a highly desirable neighborhood.

Be sure that you are purchasing in a desirable location though.

Usually you're going to have to invest some front-end money to survey it out and work with an engineer to figure out what's possible (generally the more lots the better) based on your existing access to infrastructure, the desirability of the area, zoning rules, etc. 

To add more weight to your case, dig deeper into local records.