Now it may not be every investors cup of tea, but there is substantial profit at each step.

Simple, lower the price if you are no longer “in no hurry to sell”.A couple of points...There is no such thing as a “performance guarantee”Not sure why You think the CMA is bad...you agreed the comps were valid, and I’m not sure what your inexperienced “standards” might be, it’s not something you’re going to persuade a buyer with.Raw land does take a lot longer to sell.If the land has odd boundaries, then the Owner should put out some approximate boundary markers.Listing agents don’t go to most showings.And of course, how much your grandad would need to make his life easier has no bearing on what someone might pay for it.

The first candidates are inexperienced and as others have noted their rent would be doubling in moving to your property.

sometime you do get lucky enough come into some motivated seller when u offer the hard money and quick closing. or some inexperienced listing agent that underdetermined the value off property

There's a lot of moving parts and a lot can go wrong for inexperienced investors. 

The seller when they can’t find a buyer and the buyers who are inexperienced investors desperate for a deal and insufficiently educated on how to identify a good deal.

Are there clues how to read the tea leaves here to approximate an amount-need to know how many cashiers checks one might need to bring for shopping?

@Leland James if you're inexperienced, you'll have a hard time finding a private lender willing to take a second position lien on a property.

I think, at this point I am too inexperienced to aim for this kind of loan.

I think if your partner is also inexperienced that would be a recipe for disaster.