Reimbursable Owner Expenses Paid by HOA

You could do one of two things.

1) Ask the vendor to bill the owner separately. They may or may not want to do this.
2) Invoice the homeowner, have them pay the HOA and the funds would then pay the landscaper. Run it as misc income and misc expense and the books balance.

It sounds like neither the member nor the vendor understands the contracts each has with the HOA. Tell the vendor to bill the member directly. Someone should speak with the member and tell him or her what's what. Also check and see whether the vendor, while working on the member's courtyard, was somehow using time that was supposed to belong to the HOA. Get everyone involved here on the same page.

I'm with the others who say to have the vendor bill directly, assuming the association did not give prior permission for this arrangement. The vendor should be made to understand they are free to work for other customers, including homeowners, but that the HOA will have no involvement.

The landscaper billing the association for work done for a homeowner is no different than me walking into a Mercedes dealer and telling them to bill my car to Johnny Depp and I'll reimburse him.

That pretty much lets the landscaper off the hook since they were operating under the direction of someone in a position of authority with the association.

Yeah I kind of smell something funny on this one. Sounds like someone tried to funnel the money through the HOA. Think this actually akin to money laundering?

Our HOA was responsible for lawn care. However, if you wanted your bushes trimmed or other landscaping done, you paid the contractor separately. Not through the HOA.

Note: I would want to keep an eye out on this President... Not sure how long they have been at this. You could be feeding a rat...

I would tell the contractor to bill the owner directly.

I'm thinking that this contractor might have a residential department and a commercial department.
If this is correct, then it's likely the commercial department wasn't supposed to do this work and this is the way to make there books work.

As an example, at one time our common area was being maintained by a national brand lawn company. A bunch of owners got together and, at the homeowners initiative, entered into contract that when the company does chemical application or seeding to the common area, they do so to the group of homes that entered the contract. Well, the residential group comes by and tries to drum up business. In fact, they took samples and told me that they could do better then the company I had now. I politely asked what would be different. They went into their sales pitch. I then said that I asked because it's their company that is providing the service now. Bottom line - our group of homes were not allowed to renew our previous deal.