My own listings market better than my agent's, so is it time to bring it in house

At nine deals I'd keep it. Not for the $500. The reason is that you're still learning what your buyer pool responds to, and you learn that by writing the piece and watching the showing traffic. Hand that off now and you outsource the feedback loop before you've read it.

I hold land, which is a different animal, but the pattern's the same. The first several listings I wrote myself taught me that buyers on my parcels care about one thing and my agent thought they cared about something else. I'd never have found that out from a provider's deck. Hire it out when you know the answer and you're buying execution.

@orchard's feedback point is the strong one but I'd push on @keystone's $500. You valued six hours at your acquisitions rate, which assumes the six hours converts to sourcing. You said yourself that on a bad month it converts to nothing. So the honest cost of path one is somewhere between $0 and $500 a listing and you don't know the distribution yet across nine deals.

That matters because the whole case for paying $1,400 rests on the high end of that range being typical. If it isn't, you're paying $1,400 to buy back hours you weren't going to monetize.

Different angle. Whatever you decide, look at what your agent's brokerage requires on materials produced by someone other than the listing agent. Advertising and attribution rules for listing content sit with the licensee and vary by state, and some brokerages have their own review process on top. I've seen a perfectly good flyer get pulled because the required brokerage identification wasn't on it. Ask her broker what they need on the piece before you spend $1,400 on one, and get the answer in writing.

On the substance, @keystone, I'd structure path two as a test rather than a relationship. Two listings, priced per listing, no retainer, and you keep the working files. If the compounding argument is real you'll see it on listing two. If they lead with design quality in the pitch, they'll lead with design quality in the work.

Reading this the thing I notice is that neither path fixes the actual gap, which is that your agent's marketing is a template and you're subsidizing it. You're paying a full commission and doing the marketing labor. That's the number I'd renegotiate before I spent anything.

I don't have your volume so take that for what it's worth. But if she's good on price and negotiation and bad on marketing, that's a conversation about her fee, and either she brings a real package or the fee reflects that you're bringing it.