(we'd write a dog security deposit equal to that cost into the lease.)

Security deposits  

In a smaller scale, this is why landlords try to collect as much money upfront as much as possible (e.g. security deposits, first month's rent, last month's rent, etc.). 

I don’t mind paying a fee once I secure the lending. 

The property must be the only security for the loan.

Thing#2 - Use your owner occupant status to its full benefit (Low down payment-Lower interest rate, etc) and buy your next rental property now as an owner occupied home and live in it for a year or two while saving for rental property number three - Buy rental number three as an owner occupant and live in it for a year or two while saving for rental number four .... and so on.You see that your wife will need to be onboard for this to work out - You will be buying a home that is possibly not quite what she may have in mind for your "forever" home and there will be occasional moves as you acquire new investment properties - Eventually, you will not be able to continue this technique and you will get to buy that "forever" home.  

For example, find a secured loan @ 12% for 12 months or less. 

Form an addendum that Jack and Jill sign where Jill acknowledges she will be taking over for full rental payments, damages to the property, and security deposit (would not recommend giving half back to Jack you could argue this would cover him getting of his lease agreement early).  

So maybe by doing it outselves will be a better option with the help of subcontractor, the next time.The reality is that I am the one intereseted in not losing money because is my business, the contractor does not have a problem with the time, he has his money secured. 

I think master lease at least provides you with some sense of security on getting the money on-time, headache-free.