What combination of pieces you use is of course up to you, but here is one possible scenario:- An initial touch using a post card with a simple message- A white letter of no more than 2 pages wherein you explain how you can help the recipient with your unique set of skills.- A final touch, this one could be another post card, a short yellow letter or a 1 page white letter.The idea is to provide a simple initial message, expand on that message and then reinforce the urgency of the message.

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. 

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.

Unless you're looking to start a job as a landlord of your own deals and hope to be financially free by the time you have grandchildren; you'll need a better plan.The vast majority of highly successful real estate investors use a combination of the I and B (or S to a lesser extent) quadrants (read RichDad's Cash Flow Quadrant) to accelerate the passive income and wealth accumulation real estate done well can provide.What source of income do you have now to funnel into real estate?

I utilize a combination of the two.