But despite all the planning and experience filling my sails, pointing my bow away from land and towards the horizon has been one of the hardest things I've ever done. 

If you have a long time horizon the market cycles are much less significant of a factor. 

And I'm guessing you want to speed up that 40 year horizon?

Young investors with a long time horizon can do well to use leverage to build equity over time, Older investors like me who need to invest cash will need to go to lower priced homes to get better returns.

Rent Breakeven Horizon: Full Weight (~5.33 Points)Note: The “breakeven horizon” is defined by Zillow as the point, in years, at which buying a home becomes less expensive than renting the same home.Share of Young Homes: Full Weight (~5.33 Points)Note: “Young Homes” refer to housing units built between 2010 and 2016.Building-Permit Activity: Full Weight (~5.33 Points)Note: This metric measures the number of unit permits pulled per 1,000 residents.Affordability & Economic Environment – Total Points: 20Housing Affordability: Double Weight (~5.00 Points)Note: This metric measures home price as a percentage of income.Maintenance Affordability: Full Weight (~2.50 Points)Note: This metric measures maintenance costs as a percentage of income.Population Growth Rate: Full Weight (~2.50 Points)Job Growth Rate: Full Weight (~2.50 Points)Unemployment Rate: Full Weight (~2.50 Points)Underemployment Rate: Full Weight (~2.50 Points)Median Credit Score: Full Weight (~2.50 Points)

It doesn't have to be money, having another job in the horizon is always a good incentive for contractors to waive their estimate fee.

You landed in the right place to learn and expand your horizon in Real Estate Investing.

@Brian S. waiting till you get a deal on the horizon is a good idea, but it you want to be able to execute faster I can suggest bundle the mortgages you have under one portfolio loan (as suggested by @Jerry Padilla above) and then open a "Line of Credit" with the same bank.It acts like a credit card, and you do not have to pay any fees if the money not used (some ask for yearly fee of $50-$100).

With that said it will take me 3-4 years to get my money back out of the home which is a reasonable horizon.

Every reliable indicator showed a 9% to 15% drop on the horizon for March sales.