We lost about $100,000, which we had borrowed from family.

So give those folks the choice...go pick veggies or lose your welfare payment.

And 3 days a year I spend about 30 minutes pondering a repair, rent increase or turnover choice. 

My question again stems around using seller financing to allow them to receive a consistent monthly pay of X amount and delay/lower their tax bill in the short term instead of going through a lender to borrow 800k+ causing my mortgage to be significant part of our income roughly 40-50% of take home -  which we are approved for LOL.

@John Jacobs I require my borrowers to have policies that cover replacement cost. 

My borrower is irate as it has been 2 months.

Their rates are good but boy, they looked at my financials and ask some funny questions such as asking for proof that I could withdraw funds from my SEP IRA account, and that I need to provide documentation to verify that  this employer sponsored retirement account allows for funds to be withdrawn, or if withdrawals could only be made in connection with the borrowers employment termination, retirement or death etc. everyday they sent me something new to answer.

However, the LTV that you will be allowed to borrower will be less, in the 60-70% range max.

For what you are trying to achieve you'll want to stick to the suburbs and a few choice neighborhoods on the West Side of the city.

So choice is staying stock market and making 15%-20% or buying property and MAYBE breaking even.