At a certain point, the 7% interest (assumption) I can make on the investment of the profit of sale of the rental exceeds the amount I make combined in cash flow, principal pay-down, and 1% appreciation. 

If so what elements is the tenant in charge of?

Note: The low bid is NOT always the one to go with, price alone should not be the defining criteria as the basis or your decision to hire any one of them.Reputation, bonding, experience, schedule, timely responsiveness and the way you can or can't communicate with a sub are all elements that should be included and weighed in making your selection to hire each sub.Last and certainly not least, MAKE SURE YOU REDUCE YOUR AGREEMENT WITH EACH SUB TO A WRITTEN, CLEARLY UNDERSTOOD AGREEMENT.Since you appear to be new to this game, ask each sub to provide you with their version of a contract to accompany the bid they give you.

@Sadrud-Din WilliamsThere are key elements for success regardless of any specific investment, such as individual determination, knowledge, networking, hard work, access to capital, luck, and timing.

In that situation, the gamble of the combined storm factors seems less with non-bridge debt.

Since you're combining strategies, with one large goal to take care of your family, I'd worry less about the financial sense of the deal and more about the life sense of the deal.

For purposes of this definition, an individual or entity will be found to have engaged in a pattern of business if the individual or entity by itself or with any combination of other individuals or entities,whether as partners or common owners in another entity, hasengaged in one or more of these practices on 2 or more occasions in any 12-month period."

Tired boomer + landlords that own free and clear are my favorite SF seller as well.Travis- tough to combine proper SF with no capital. 

This means the less cash you spend to buy the property, the less you have at risk.Based on your complete statement above, the reason why you lost everything had more to do with your lack of knowledge on how to analyze properties, and all the mistakes you said you made along the way.After ten years, using a combination of reinvesting the cash flow (part of it) and exploiting the compounding effect, the REI that only paid $20k for the same properties the other REI paid $100k for, could have had 43 properties and $215k/year in cash flow. 

Various combinations of the following I have considered.