Take a realistic view of what can be accomplished.  

For instance; depending on the price range of the unit, people may be buying a place to call home; or they may be buying a sense of security that is economically stabe and affordable; or they may be buying, in the case of a luxury rental, prestige and a sense of accomplishment in life.

A typical cross collateralization may also be able to accomplish what you need, but I would not be using the 100% financing language as it indicated more risk than what you're actually looking for. 

My sister and I are not opposed to some sort of buy in as well, as it would likely help my father clear up some debts, and would just be nice to help him realize some sort of lump sum gain, in addition to what would likely be a share of monthly rental income.We are looking at setting up a trust to accomplish all of this, but are just at the beginning of this journey. 

Hey @Ashley Payne - I think the question of whether or not to sell really depends on what you're trying to accomplish. 

I know here in Chicago this is pretty tough to accomplish in some of the nicer areas.

I have my money on the guy making moves over the guy with the perfect plan to get further, get to FI faster, accomplish his goals.   

You don't lack motivation, you lack clarity, I personally think a good coach will help you with what you are trying to accomplish.

It's amazing what you can accomplish buying one or two deals a year of boring cash flowing deals.Most investors don't have the patience or the discipline to buy an asset, and manage it and hold it for long term.

What you’re trying to accomplish is possible but circumstantial, what I mean by that is you’ll have to review the lending paperwork to see what events change the course of your traditional loan.