Strategies for Seller Afraid of a Huge Tax Bill Selling Portfolio

[Austin Hughes]

I need advice on what options exist for this seller OR what I can say to make the deal look great to the seller. Here's the situation:

I've been working with a seller who owns 13 properties which I'd like to buy. He is open to the idea (somewhere in his subconscious) because he took me to each of his rentals one by one and gave me numbers and info on them. 

He mentioned he would sell for below tax appraised value, which in my area, tax value is usually 20%-40% below actual value, so this would be a killer deal on 13 houses. I could probably pay more than what he wants and still have a solid deal.

After talking a while, he pushed back and said he really didn't want to sell any, and if he did, he might just sell one, because he is very opposed to jumping up a tax bracket. He had been complaining about how much he pays in yearly property taxes ($35K) for these houses.  He is very old (94 yrs old) and he absolutely won't owner finance. His wife is a little younger (early 80's) and doesn't want him to sell, because she likes rental income. (Before you guys jump on me, this guy is as sharp as a tack, and I would never take advantage of an elderly person anyways.)

SO... What angles can I approach this from? Are there tax sheltered methods for this man that would help both of us? Is there a way to frame the conversation, so the large tax bill seems less daunting?