While not a written rule  you or having your PM contact the tenants prior to you taking ownership or w/o the expresses consent of the owner, or doing a walkthrough etc....is seen as bad form.  

Second, in discussing the matter with the Tenant, I tell the Tenant that I don't agree or consent to the Tenant moving out early and that we will handle the matter according to the Lease.

Similarly, a credit check will allow you to assess the prospective tenant’s likelihood to pay rent reliably.No reasonable tenant-to-be should resist providing relevant information, giving signed consent and paying the application costs associated with renting a home.

I know if the person is listed as a trustee I could directly mail to them, but I have been encountering lots of homes that are listed as John Smith Revocable Trust, or John Smith Non Revocable Trust, where I believe that the person who owns the home may either be deceased or towards the end of their life. 

In Chicago you as the landlord are able to enter the rented apartment without consent if its an emergency situation (pipe broke, fire...) otherwise you have to give a 24 hour notice.

other investment opportunities (other than a flat out loan at a favorable interest rate) seem pretty fraught with peril as you will need your sister's consent and participation to take any action that would allow you to realize any gain, including a refi or property sale.   

You cannot text unless the person has subscribed and given you consent for that communication in MA.

As long as you're reaching out to people with the information they want, and you have consent to message them - a mass texting service can be a very powerful communication tool for delivering reminders, notifications, and alerts.

It also may not be tax efficient to do this and you may be better off creating a transfer of death designation (if your state law allows it for real estate) or placing the property in a revocable living trust.

I have been reading that in order to contact a tenants previous landlord, especially when it involves reaching out to a large property management company/apartment complexes that they will sometimes ask for a tenant release of information consent form.