That takes time and effort and expenses for due diligence that should be set off by the sale price and I doubt he will look at it that way.You'll get a better deal by making an offer on the whole mess, not cherry picking.Are these to flip or hold, determine that on each property. 

We have one in Marathon too..calls the cops if someone sneezes too loud.Feel like the vacation rental market is generally a bit under appreciated by investors and a huge opportunity for those willing to put in the extra effort.  

While walking in my journey to grow and learn more about investing I stumbled upon a book on real estate after the first few chapters I immediately knew where I had to focus my effort on.

Do any of you set time limits for people in an effort to move forward?

The risk levels, the work/effort levels, the capital levels, and the skill levels required are on two totally different planes.

Not a closed deal, just the simplest "Please tell me more".Driving for Dollars is a low return also due to even finding a prospect, they may not be home at the time of your discovery and then need to return or call (if the phone number is available).I don't like wholesaling for other reasons, but pouring this much time, effort and money would discourage me too. 

Instead spend your money and effort on good insurance.  

Sellers do not want to go through the time, effort and exposure, or tie up their property, in a transaction that has no chance to close.There are those extremely rare cases, that become real estate legend, in which a buyer with little capital, and no borrowing capacity, is successful in convincing a seller of a large, expensive property to take him seriously and is able to perform a high wire act of raising capital from a variety of unconventional sources and actually complete the purchase.  

Next I plan to try to find a contractor to walk the property with me in an effort to narrow it down!

It's called networking and marketing along with a being consistent with your efforts.