The question then becomes: how likely is the lender to exercise that right?

This person will be critical in helping you find the new listing quickly.Repeat this exercise 10 times or so without making an offer. 

What we do look at is how much rent we can get each month, how much of an option for the property we think we can get, how much money will be left in the property after we get a loan on it, how much cash flow we will get each month, and how much of a profit we will make when the tenant exercises the option.  

We've decided to go in a different direction with Property Management, and we're going to exercise our X day notice now with a last day of X.

They exercise the newly assigned option and use their $20K + ($500x36=$18K) as their down payment. 5.

That fee only becomes their down payment if you agree to accept it as such when they exercise their option.

One thing no one has mentioned in this thread is the value of the time you are spending on this exercise. 

To Tim's point about buying in your own name and transferring later, I've heard the same that banks rary exercise dur on sale clause, but it may be worth asking upfront to get a feel from the banks you're dealing with on whether they'd give you a hard time on it  if there is a local meetup or RE Investing Association, try to attend so you can see who other investors are using for their commercial loans.

After all, if you are working 24/7, and you never get a break, you are just going to get run down.If you find you struggle to mentally unwind earlier than you’re used to, try some tricks, like putting away electronic devices an hour or so before bedtime, reading a book right before bed, and making sure your room is very dark so you don’t get distracted.ExerciseYou don’t need to take up marathon running to get the benefits of a consistent exercise routine.

Canceling the contract without proper justification (those reasons should be spelled out in the contract) will get you sued for "specific performance" and/or "fraud in the inducement" and the seller may well look for consequential damages.Proper justification for canceling the contract is normally limited to home inspection and mortgage approval.