Makes me not have confidence in the calculator. 

I live and work out of Orlando, FL but travel the U.S. to meet with landlords, builders, flippers and all kinds of investors.  

My example is that one of my partners wants to sell a property that he owns individually right now TO our joint LLC (he is getting older, wants to travel and have less responsibility).

Finding buyers is easy, but it's also a confidence booster. 

I have been to seminars, joined mastermind groups, and can confidently say I have one of the best mentors in the business.

I would log in to airbnb as a traveler and see what how many properties are listed, their listing price, and view their calendar to see how booked they are.

And many did get rich quickly after the crash...which creates unrealistic hope for another similar historic opportunity and unwarranted confidence that we will pull the trigger when the market is in chaos.

I am currently travel nurse in Norcal and have been in the area for 7 months (great area) and I can tell you there are always needs for rentals for travel nurses.

My point is don't be overly confident in your position and try to work with her in good faith on a solution that works for both of you.It is actually not the worst time of year.

Try breaking down what it is that is causing you to experience 'fear' in taking action.Try setting yourself smaller commitments that will get you towards your goal and list out what the risks are and how you might mitigate them.An example of a commitment would be to make x offers per week on target propertiesBreaking down a risk might be something like-Risk - target rents not achieved-Action/Mitigation - analyze comps to give you more confidence in the rental rates, model the deal more conservatively so that you can see if it works with lower ratesetc.Do a bit of research and I am sure that you can find lots of actionable help on how to overcome fear of taking action.