I've got a rental home that I'm willing to sell. If possible I'd be interested in a 1031 exchange to several acres of raw land, eventually wanting to sell our current homestead and build new homestead on the raw land. Is a 1031 possible in this scenario?

I'm pretty sure you can't 1031 into personal property. Has to be like kind: another rental property. Check with a 1031 person though, maybe there is a loophole.

I considered something similar recently.

My CPA told me I would need to wait 2 years before breaking ground (something about the primary/homestead rule only applying for that amount of time), and I would need to be capable of proving that my original intent wasn't to use the land for my primary residence. His suggestion was to look into subdividing. That way, if the IRS ever asked, I could show them the plans and simply say that it fell through.

Sounded like a lot of work. That, plus the impending increase on capital gains tax, was enough for me to decide to cash out instead.

Land and rental property are like kind. It may not be an investment if you plan to exchange for something that you will use as a personal residence, which would disqualify it under 1031(a)(1) since it's not for use in a trade or business and not an investment at that point. Sock's CPA may have been referring to a 121 exclusion, which excludes a portion of gain if you occupy the property for 2 of the last 5 years.

My answer is no, that exchange won't work and you should pay the tax on gains (after properly cost segregating so you minimize recapture and determining total basis). Buy the land separately. That advice is worth what you paid though.