Will they be prepared to address retirements and disposition?

If you're near a medical and/or law school, monthly rentals are preferred by those who are preparing for board exams over vacation rentals as well as by visiting professors. 

The contract stated this could happen but preparations for it were practically non existent.

Will they be prepared to address retirements and disposition?

Hello, My name is Matthew I'm new to real estate investing and am currently looking to start off with a rental property to get started, having done a lot of reading and research on my end I'm still looking into getting a better understanding and more knowledge so that I can be as prepared as I can be.

That being said, here’s what I would recommend for a thorough DD process:-Build a plan in advance (setup a spreadsheet, meet with the team, etc)-be prepared to take a lot of pictures -document notes with each room (we use notes on Apple and share it with the team)-align the team on standardizing information (example: what does “bad” mean, what does “okay” mean, etc - everyone looks at things differently and you want to make sure the notes are accurate during your debrief)-bring in professionals for things you can see, like sewer lines hope this short list helps! 

It is the most popular software in the industry, and most Tax Preparers are familiar with it, which makes tax season easier.My Recommendation: Spreadsheets are usually fine for your first 1-3 properties. 3+ properties, you should use a software.

Be prepared to explain why the extension is necessary and demonstrate your commitment to closing the deal.

It is a business though so be prepared to work but the ceiling is very high. 

If the property is vacant, most lenders will use the rent schedule that the appraiser will prepare as part of the appraisal process.