Hi @Austin JonesI'm a certified ProAdvisor for both QuickBooks Online (QBO) and Xero.

Never had to do this ever before  There are two ways to do this, google and find a template online or get a realtor that can use some promulgated documents by TR.Per law, no-one can write you a legal document except for an attorney or the person providing the document will be infringing the law.In terms of the tenant leaving there is no point to pursue any legal way and for you to get possession, you create a termination notice and then in 30 days you can take possession.

It offers online rent collection, expense tracking, tenant screening, and more.Zillow Rental Manager: Another free option where you can collect rent, screen tenants, and even list your property.Background Checks and Lease Agreements:Avail.co: This platform not only allows you to collect rent but also provides comprehensive tenant screening, including credit, criminal, and eviction checks.

Go to Etsy and search for "rental property tracker," and you will find hundreds of nice spreadsheets to track 10-20 rentals, usually for under $10.Software has extremely helpful features like online payments, marketing syndication (click a button, and your property is advertised on multiple sites), electronic document review/signing, maintenance tracking, and owner reports.

I'm browsing online listings and want to understand how to dissect these deals before diving in.

My brother's rental is a little over 1,000s sqft heated living area, so the ADU would only be permitted for 500 sqft in Winston-Salem, according to information I found online .One advantage of an ADU I believe would be the ability to hook up to the primary residence's utilities. 

The industry is changing and new services are coming online to help owners and property managers to streamline this process.  

Are online webinars as good as in person meeting? 

Check reviews of them online and ask for references if they are willing to let you speak to their previous clients!

You can list your property at the local Housing Authority and I think some have an online database of rentals, but we've never used that.