How do you connect with the right contacts or organizations to offer your property for mid-term rentals?

I recommend starting by contacting the county’s property tax office to determine if they are open to discussing or reviewing an appeal for property taxes.

I did try contacting the local  section 8 office but didnt connect to anyone yet who could help me.

Ideally, this CRM would have the ability to have up to 500 contacts, at the very least. 

HI ReetiI would 100% recommend contacting local professionals in your chosen markets. 

.: It's not an issue IF their lease is scheduled to expire.My personal practice: when a tenant submits an application, I let them know I intend to contact their former landlords.

I'm contacted all the time by people that want to do what you're doing. 

There is no harm in reaching out for a slight difference in budget you can just say that you got there contact on FF and have an available unit slightly above their price range and tell them the price and let them know to get back to you if they are interested.

Oh also number one skill to develop regardless of the route you take is being able to identify and get in contact with motivated sellers.

You can also list on Facebook Marketplace, join local Section 8 Facebook groups, or contact CMHA directly - they often have a list of people looking.