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.

@ David Ounanian WOW that is some crap!

Once the units get bigger, you may need something like one window unit per bedroom; people don't always want to leave all the doors open so one unit can cool the whole place.If there is more than one window unit per unit, and one of them craps out, you usually have the option of shuffling a working one into the bedroom(s) and then getting a new window unit tomorrow. 

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.