It seems like another option here would be some type of 'life estate' type arrangement....instead of death it would be kids being a certain age.If for example you could buy sub2, and pay the husband $550K now.

Dirt and some flowers in

So the asynchronous nature of tenant requests, coupled with trying to get them handed out to the right handyman, plumber, etc, are driving me insane.Is this something that can be outsourced without going to a full 3rd party property management arrangement?

I made arrangements to fly to Charleston from Portland Or for the sole purpose of Meeting this new Banker  and showing him all the projects we had done there.

I want to give them some time to find other living arrangements or even perhaps considering renting to them.  

It's hard to say Russell, because we don't have an arms-length arrangement when the buyer is representing himself/herself as agent. 

Each LLC can have a separate agreement, but the IRS will scrutinize this, so keep everything above board to avoid issues.Tax Implications: This arrangement could allow you to shift income and claim home office deductions, but it needs to be done carefully to avoid triggering any red flags with the IRS.Renting a Car to Your LLCs:Renting your car to your LLCs can also offer some tax benefits, such as shifting income and potentially deducting expenses like mileage and depreciation.

However, few realize that the high cost of housing and related expenses may bring them back to shared living arrangements in the future.Is this a good thing for individuals and society?

I would also make sure that he doesn't sell his part for at least 3 years.What do you guys think of this arrangement?

In my past professional life I worked as an attorney for a hotel development company that owned over 1B in assets yet as a company we  did not feel the need to utilize entity structures nearly as complexed or  convoluted as what you arranged.