I think if you have a valid reason then the lender may be more flexible. 

Best to be flexible and also best to set the expectation and stick to it.

Maybe renting would give you the flexibility to time it right with your financial situation

Most of our rental pool are younger, older with fixed income, not permanent residents or people who can not qualify for various reasons to be buyers...or do not want the hassle of owning and like the flexibility of renting.The homeless thing is disingenuous I think to a degree. 

If you can STR some of the time, then you can be flexible with your begin and end dates.

If the seller is experienced, he or she may request a higher interest rate, or less flexible terms - the point is, it's unlikely you'll be able to get the perfect storm for financing like above. 

I am eager to learn, and flexible in terms of real estate markets. 

I think a good knowledgeable independent broker has more flexibility to help get the deal done. 

@Tom Brickman I use local banks because they tend to be more flexible.

We aren't going to let future tenants do that and we won't be as flexible in the future,  so we learned a lesson and that is our learning curve.