I have a pretty good grasp of the market here. 

Couldn't grasp the hang up and was told we just didn't understand the situation. 

Ok so I grasp how whole life works.

But my takeaway from your post, which is clearly directly at newbies, is the need to have knowledge or grasp of all the issues before getting started, to which I strongly disagree. 

I feel as though that is the hardest part for most RE investors to grasp.

Many investors do not grasp this concept and believe they have a positive cash flow property when in fact once they apply a return to the equity they are left with negative cash flow on the property itself.

Ask a lot of questions and get yourself comfortable with when to make offers, how to make offers, how to calculate cash flow, how to calculate cash on cash returns, how to calculate cap rates, how to estimate ARV, etc.Once you feel like you have a great grasp and action plan on how you will operate your business, it's time to start taking action!

I don't quite have a firm grasp of the 50% rule that I've seen you all mention and not sure how to apply it to homes that are purchased with cash?

I have a good grasp of valuation on most all other commercial asset classes, just not sure what I need to tweak to accommodate hotel type asset.Thank You! 

Find someone at a bank that fully grasps what you are trying to do and who works for an institution that does these types of loans.