I won’t include them in the costs since they should increase the value.I will also be careful of property managers who mark-up maintenance costs in addition to their regular fees.

If you plan on buying additional homes with this person, I would just let her enjoy this easy sale because the next one might be much more difficult. 

In addition to above, the lack of core investment opportunities, and inadequate inventory for proper diversification are critical issues that the industry needs to solve.At the same time, I don't think all of them are going to end up in a ball of flames.

I simply add something like the following to Block 20 ("Additional Terms"):"Buyer reserves the right to finance a portion of the purchase price, but is not requesting a financing contingency".Obviously, if your financing falls through in this scenario, you are obligated to cough up the cash to close, or lose your deposit.

During this time we can decide if we like the area, while searching for other areas (perhaps less touristy) and if so, purchase an additional home in a traditional residential area and use the "vacation" home as a rental?

The house cost $80K, the first renovation was $57K and enclosing the patio was an additional $12K. 

In addition to managing properties I have a background in Marketing and can honestly tell you that lead generation isn't a magical fix-all term. it's a lot of hard work and often a big investment is needed to start seeing results.

Maintenance is an additional cost. 

Any additional inputs are very much appreciated!

Additionally, when talking "Cash on Cash" and Cap Rates with other investors, is it typically assumed that a Cash analysis on Cash includes the types of expenses I list below?