If you don’t pay the tax when you transfer the stock to them they’re going to owe the taxes on your gain and you haven’t really “paid them back”. 

If I did this, I could then transfer the land to my LLC or allow the LLC to lease the land from me for the storage facility2.

You might be able to get around the fact your entity owns the property by either transferring the property back into your personal name or by some personal guarantee or cross-collaterization agreement.

Upon her passing, the 401k interest was transferred to me into an inherited IRA account at the same servicer.

They will likely have interest when you want to transfer ownership of the property to the new LLC.

So if I was dealing with a seller who was insisting on handling the transfer this way, I would be wondering what the seller is trying to hide... and I would figure it out.

Here’s a method of transferring ow worship that worked for me.

We were being transferred to that area and went up to look at a couple different homes in the area and that one came up that day, and we made a full asking offer immediately.

Most people will get the loan in their name first, and then transfer it into the LLC after.

It’s worth noting that they can also provide some flexibility by avoiding direct ownership transfers.