As a tenant myself, who is just about to buy her first property...landlords who are responsive, friendly, and actually care when I have an issue make me very happy.

Sometimes building trust with Private Lenders take some time but if numbers make sense, you won't have issues having money follow. 

Personally, I would walk away, but he's emotionally invested, so, I'm trying to give him at least some tips, where he should ask for changes in the contract, which probably won't happen. 

@Bradley Cumming one issue with your plan is that you need "good" credit to refi!!

Good  tenants should have no issues with a M2M lease.

Of course the answer to this issue if you close late in the year and want the full 180 days is to file an extension.For you it is irrelevant whether you sell and close the purchase in 2016 or close the sale in 2016 and the purchase in 2017.  

I have had numerous businesses through the years but it was serious health issue and the realization that disability social security payments would not allow me to live that made me want to build a successful RE portfolio.

Remember to leave emotion out of it and think "Future Rental".

Our lender also informed us that the biggest issue that raised the red flag and qualified the property to be in Below Average Condition is the detached garage which needs major repair.Our dilemma:Our lender gave us the option to buy the property all cash and refinance instead of it being considered a purchase.

If you have " small maintenance " issues and need to get a loan , whats going to happen when the tenants dont pay ?