I am looking at two properties where the same lease option structure might mean opposite things for my exit

Your attorney is right and I would not budge on the two-document thing regardless of what the sellers expect. The sellers expecting one piece of paper is a negotiating position, not a legal requirement, and it is your neck on the line when a judge decides whether a lease default extinguishes your option. I had a similar pushback on a duplex in Garfield Heights last year, seller's agent kept saying "this is just how we do it here," and I said fine, here are two clean documents that accomplish everything you want, sign both on the same day. Nobody walked.

The Candler fourplex is the one I would actually spend energy on right now because an $8,000 to $10,000 option consideration on a $410k asset with comps moving is a small number if your 24-month read is right, and the two-document structure protects that consideration much better than a single instrument would. Fayetteville at $12,000 over recent appraisals with a $4,000 to $6,000 consideration ceiling is thin. If the market softens even a little you are holding a ceiling that is already below current appraisal value, which means your sandwich spread starts underwater before anyone moves in. What are the actual recent appraisals coming in at on Fayetteville, like the last three comparable sales in that pocket, because $198k over market in a buyer pool that only supports $4k-$6k option money sounds like you are absorbing the seller's pricing problem?

Your attorney is right, and the Decatur example you cited is exactly why. When the lease and the option live in one document, a judge can read the whole thing as a single instrument, which means a lease default can extinguish the option. Keeping them separate is not a stylistic preference; it is the structural protection. The sellers expecting one piece of paper is a negotiation problem, not a legal reality you have to accept. Most sellers who push for a single document have just never seen a well-drafted two-document set explained clearly. That is a conversation your attorney can help frame.

On the question of which to work through first: the document structure is the same regardless of which deal you do, so you can resolve that piece now and apply it to both.

The two deals do have inverse risk profiles, though, and you have named them accurately. On Fayetteville, you are selling a fixed-price ceiling in a market where you believe the asset is already $12,000 over value. If you are right, your tenant-buyer's exit may fall apart at the appraisal stage, which puts you back in the deal at the worst moment. The $4,000 to $6,000 option consideration you collect is real money, but it does not fully offset that exposure. On Candler, you are paying $8,000 to $10,000 for the right to benefit from appreciation you believe is already moving, and the rent spread on a fourplex can help carry that cost while you wait.

I would want to know one more thing before treating these as equivalent decisions: what does your 24-month rent income look like on the Candler fourplex relative to what you are paying the owner, and does that spread turn positive before the option expires?

What are the lease terms the Candler seller has proposed?

The document question and the deal selection question are actually independent, and treating them as a sequence is slowing you down. Your attorney is right on the instrument separation, and that position should be non-negotiable in both deals regardless of what the sellers expect. One piece of paper, in the jurisdiction you are describing, is a structuring risk you have already watched materialize. The sellers' preference for a single document is a negotiation point, not a constraint on your legal structure. Confirm with your attorney how Georgia courts have been treating combined instruments recently, then hold that line.

Now to the actual structural difference between the two deals.

On Fayetteville, the assumption doing the most work is that $12,000 over appraised value leaves you room to build a spread. If your tenant-buyer's purchase price needs to clear your strike price plus your margin, and the market in that pocket does not move, you are absorbing that overvaluation. The $4,000 to $6,000 option consideration you collect is thin cushion if the deal unwinds. The ceiling risk you named is real, and it compounds if the buyer defaults late in the term after you have already credited rent toward a price you cannot renegotiate.

On Candler, the assumption doing the most work is that the comp trajectory holds across a 24-month term. Fourplex comps moving fast in one direction can reverse, and your $8,000 to $10,000 consideration is gone if you do not exercise. What is your plan if the appraisal at month 22 comes in flat or below your strike?

The risk you have not mentioned: on the sandwich structure at Fayetteville, your tenant-buyer's ability to actually close at term. If they cannot finance out, you are holding a lease with no exit and a strike price you are still obligated on.

What is your fallback position on Candler if the spread compresses and you decide not to exercise?