But let me start at the beginning.My wife and I are about to retire.

I also am making assumptions that by this point, not all purchases will be one home at a time - I'd like to explore purchasing in bulk from retiring investors, or other strategies to get a number of properties at once.

Unless you plan to retire and do a cash-out refi and then live off the loan as opposed to income. 

I recommen connecting with @Zach Lemaster, CEO and owner of Rent to Retirement.

But i do have a decent amount of equity in my primary home and some money in my retirement account. 

We are retiring in a few years and will likely make less than that next year. 

This time around the seller was retiring and moving so he was looking at selling it quick to get some cash for his move.

If your goal is to become financially free quickly, your best bet might be to sell and buy something you can house hack but if that isn't an option, keeping this house rented for the next 10 or 15 years could essentially retire you so long as you can find a way to avoid losing half of it to taxes. 

He gave me three scenarios which were absolutely crazy.One was from a landlord who used to live in Paterson, NJ, many decades ago and has had a realtor friend manage the property for the last few years while they are retired in Italy.

I’m set to retire in 3/4 years and have since lost 27lbs of toxic weight (waste) and in the best mind/body/spirit shape of my life!