She is a close family member and I want to make sure we both win in this situation.I appreciate your input and would like to hear your thoughts.Best, Mike

This has always been a win-win for both parties: he is able to keep receiving income while avoiding capital gains taxes, we have been able to accumulate more property than we might have under different circumstances.After talking with several friends and acquaintances, he has now decided that he wants to put his profits in a CRT moving forward.We were previously working towards buying a parcel of two single family homes in a great location that he was going to owner finance to us again.

Win-win situation if an opportunity comes about. 

Steve Paczesny It would be a nice temporary win if you pulled off the maneuver Bill Gulley suggests.

Reuben Royal:Sales SkillsPeople Skills (How to Win Friends and Influence People)Financial Skills (Robert Kiyosaki)Investing Skills (read a cross-section of real estate books)Management Skills (The E-Myth)Hope that helps you out.Continued success!

Shoot, I was thinking of hijacking the deal but it's this investor's first deal with me and I want him to win big time.  

we thought about this too for investment properties, I agree it's tough winning houses int this market. for heloc, depending on what your investment strategy is with the property, the numbers could work. like someone else said, considered delay financing and also decision-now mortgage approval and removing mortgage contingency. 

When you’re done buying you can pay them off 1 at a time with the highest interest rate (to save the most money) or the lowest balance a(to increase your cashflow the fastest.) you’ll find that 5 paid off properties cover your “needs” and 10 paid off properties are way more than enough to live comfortably on if you’re not living the lifestyles of the rich and famous. 

The Seller wants as close to 20% down as possible and my thought was sure, since the bank will make me do 25% down, so that's a win there.

So it doesn't make a ton of sense to pay the HOA company for HOA docs on a property which you may not even win the bid on, and which they may not give you the docs for until you do.