There's this intricate mathematic relationship between interest rate,cap rate and IRRSo during QE era.

Getting freebie advice on a very intricate and personal problem on BP is not really going to serve you, any fees you pay to a tax professional is going to be worth the savings they're offering to you.

They do not "sell" the asset to the LLC they gift it/give it (which could have tax implications), but as noted in this and other posts, the LLC is not separate.

For example your grandparents passing away with the asset will be a good tax answer but it could be a bad financial answer if they are in care centers and rack up $800k in debt which encumbers the land.1st priority is likely retaining the land, debt free if possible.2nd family operating goals3rd may be tax goals as you may not have any issue until you sell it.4th may be easy of transfer but in taking care of priority number 1 you may find your best bet is to gift the asset away or put it into a trust eliminating this issue. 

I have a note to leave him in the morning, letting him know how awesome he was, and a Apple Bee's gift certificate.

He is originally from Germany and we've been presented with a great opportunity to take over one of his parents’ homes as a “gift” or possibly a small price (later discussed).

Maybe a gift card to the grocery...

I doubt I would have gifted wine had I not known that.

The estate attorney assisted me in buying out my siblings interest, had the property taken out of the trust and put in my name, and I took out a 250k (cash out refi) mortgage out on the property, paid my sibling 208k GIFT and ended up putting 30k more into the repairs.

The only negative in this situation is the one you created in your mind when you chose to look a gift horse in the mouth.