Does it need a big ticket item? 

Yes you can write them off on rentals so you’re really paying a 10-20% less interest but it’s a cashflow item as well. 

Always happy to keep an open conversation going or meet up.

Interior and exterior fully updated, important items such as heating, roof, etc updated.

Usually the cost for this is higher and the mitigation value lower, but it is still something.3) Are the areas adjacent to the property very build able, and is it feasible to increase the other property's usability if they offset support items to this area? 

The reason I am talking to him is his wife owned a house that she received during their marriage from her aunt after her aunt passed away.During our conversation, he told me that it’s been 5 years since his wife passed, but the he hasn’t filed any paperwork.

We are planning to sit down later this week but I’m thinking his figure will be 2 million or more based on previous conversation.

I establish this in my initial contact with the host, and often end up in a telephone conversation before booking.

Some providers will engage in this type of conversation; others will not. 

At the same time, I'm not familiar with items like financing debt out of a multi million dollar property and I'd rather not taking on another $3M-$4M multi-family property as my next foray into real estate.