Retired couple wanting to move to a single story home, closer to their church (which was in the neighborhood), and closer to their grandkids who live just down the street. 

My wife has recently retired and I will retire in 4 years.

(We are retired now due to his cancer).

In order for it to work for the seller, simply feel them out via friendly discussion about their life goals/plan/situation.Examples of seller situations:  -  The seller may need to pay off a large medical bill (make your monthly payments equal to the bill)- The seller may be retiring (suggest that your monthly payments would be better than a lump sum that earns a low interest rate sitting in the bank... and also reduced capital gains tax).- The seller may want to buy some "toys" ie. new car, vacation, etc.  

As far as the duplex/condo/zero lot line ideas that I have,  I feel like this is an interesting time for projects focused on low to no maintenance for the owner since you have an alignment of the first time home owner crowd and the retirement crowd both wanting the same thing.  

Case in point, the Florida cop who sat there while people were being killed, then retired with a six figure pension days later...Your tax dollars at work, don't expect too much from these GED wonders.

So if your goal is to support yourself and create a nice retirement, self-landlording might be fine.

I'm really hesitant to cash out any of my retirement investments and take the tax hit, but it might be worth the risk in the long run.

I am a retired landlord and a believer in QuickBooks who wants to help others on here know what will work for them and why. 

I have a heart for seniors and can tell you do too. (2) quick tips.Insurance is not viable, this would have to be a private pay communityLook at other providers of these kind of services ie: Hawthorn, Holiday Retirement they could give you insight in how to set something like this upFinally, when a resident reaches a level of care that requires assistance then perhaps find some caregivers that can provide assistance (check their references)Best of luck with this dream!!