I traded my new car for a down payment on a house.

If she is new to this, she will need to learn the trade and get her team in place.

Wife's SUV traded for a Prius, cash deal.  

My girlfriend's grandpa is gifting her his property.  He wants to sign over the title to her free of charge.He purchased it for $63,000 in Oregon, and is 4 years short of paying it off. Now the Zestimate says it's aro...

Here;s a guide to buying property in Italyhttp://www.detulliolawfirm.com/wp-content/uploads/...This is a good overview of things to consider when buying in Italy.Suggest that you contact an international tax attorney to determine what your US tax consequences are too. 

Eric, to be more specific on the accountant/attorney question, I was more interested in it as a consequence of potentially structuring deals an partnerships.

In fact DO NOT do this without talking to a competent CPA (who you are certain knows plenty about real estate transactions ) because there may be unpleasant tax consequences.

I mean nearly all of your time during your typical day and consequently your career.

According to IRS code 1221, a capital asset is something used in trade or as "inventory" in business.

Perhaps you could trade your skills for theirs?