This approach enabled swift action, allowing a same-day sale for $233,000.

@Brian Jordan @Dustin Heiner Interesting contrast in your approaches; however, it is obvious to me that you each have solid, well thought-out business models. 

But if you to a more wise and slow approach, you can find other ways to generate additional income, build up a 25% DP on a duplex that cash flows after all expenses and you have an EF fund, well you will sleep better at night and the odds that your investment will survive the tough times in your life is far greater then someone who sleep well at night with tons of debt who if anything should go wrong, which it does in life that person may be bankrupt. 

When I do this for the resort, I'm not getting numbers that approach the properties value.  

Do they lag behind and just use the previous month's Owner Income statement, or is there a proactive approach the moment the property is vacant?

As mentioned in other replies, I'm ideally looking for opportunities under $500k with a more passive  approach.

This approach allowed for swift action, enabling a same-day sale for $280,000.

Approach it with curiosity and you'll generally get better advice. 

and also what are your suggestions for approaching creative financing if it was not ultimately stated in listing (in other words bringing it up as an option to the seller?)

I met the association head and he's very stubborn about it.Because of the complexity of your case, it may help to get a professional to give you guidance as to the correct approach.