:) The reality is that, the reason people are selling, most often is because of a problem: ie low rents, bad tenants, too many items to fix… etc (yes, sometimes people just want to retire and move on or cash out… ) but that is not what happens most of the time. 

Do NOT mix business and personal items on that line, accounting becomes a nightmare if you do.

Is it important items such as food, emergency savings, retirement, and car insurance?

They can have the future items returned to sender.

First, determine if you are going to be replacing any big-ticket items like roof, HVAC, electric, and plumbing.

First item, liquidity.

Now the must deduct the items and time to achieve stabilization; 6 months of rent loss or an abosortion rate based on the local market and leasing commissions if ownership pays those where you’re located.

You MUST read the "insurance section" of your condo's governing documents to find out exactly who's responsible for what when property damage occurs.  99.9% of the time, the policy that insures the damaged item is the one that pays at the time of the loss. 

I think the overwhelming number of landlords would agree.The item to consider is whatever you do, you are setting a precedent that this tenant will expect moving forward.  

Items:1) Define what you mean by LIH.