Not talking about you personally.

This is our boilerplate language:Insurance: Tenant should obtain a renters’ policy of insurance on their personal property.

Quote from @Matthew Crivelli: Personally, I'm not a fan of Air B & B.

Juggling between work and personal life can be tough, but having a property manager can take some of the pressure off and let you focus on your other priorities

Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

It's not a personal sale between you and your son, but rather a sale from one LLC to another.

I have personally worked with @Wale Lawal and he is awesome. 

But I don't know your personal situation and all the financial details. 

I personally think they are “higher end” than anything stackable.

The idea of debt-free is that if a person is going to retire and has to completely depend on the income, they don't want a severe recession surprising them and causing them to default on the debt and losing the properties.In a normal world, I would do that as well.