I think you've definitely helped me get clear on my direction.

Oh man- welcome to self management.

I want to be able to send mailers directly from my CRM.

But because you rent by the room and YOU SELECTED the roommates (for which the other roommates had no control over), that makes you directly responsible to the other tenants should any harm or damage come to them.  

Nature campaigns, direct mail, text services, accounting, etc all in one place. 

They are familiar with you and can give you direction and documentation.  

Including a self-canceling clause in the note ensures the balance is forgiven upon the parent’s death.

@Andrew Steffens the pool of buyers that have six figures of cash (you really need about $150k in cash to buy a $500k STR), have some subject matter expertise, AND want to self manage is even smaller. 

Are you currently self-managing or do you have a management company?

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