To tell you honestly i can't even imagine the process..
OK, we have to be honest here... neither can we, really. Oh, we can come close, but YOU have to be the subject matter expert. YOU have to decide the right way to synchronize data between two places. It is YOUR business rules that will apply.
In a nutshell, here is the problem: You have data in a central location and you have data in some remote location. Your problem is compounded by your phrase:
office desktop is updating/entering records, site is also updating/entering records
In order to merge the work done on the two databases, you have to come to a conclusion regarding what is called "authoritative data" - which is to say, if you have different data values in two places but relating to or describing the same exact thing, only one of those values can be right. How do you tell which one? (The one you pick is the "authoritative site.")
You could not use an auto-number on the related tables at the two sites as a way to merge things, because they would potentially overlap. They would be generated in two independent places at once so without a connection, they could not be guaranteed to NOT overlap. Therefore, a direct merge with overlapping keys would probably lead to key violations.
If it were only ENTERING records, it would be easier. If there is no limitation on which records would be updated at each site, your trouble is in deciding which value in the two databases is correct. But independent updating makes it impossible to properly reconcile the two records if BOTH of their actions can occur in essence simultaneously. This is why I mentioned transactions earlier. With a transaction, you have a record that describes the change made because of the update (or perhaps explaining the update.)
I have to tell you that with 28 1/2 years of Navy experience, I wouldn't want the problem you have right now, because you are going to HAVE to control / limit how data entry and data update occur. If you could somehow set up a central database with a web-based front end, then have a shared back-end, the problem essentially goes away because the shared back-end becomes the authoritative site. But if the two machines are not connected and operate independently AND UPDATE independently, you are going nowhere.
In essence, if you can't use a transactional method, I don't think your problem is solvable by computer until you first solve it by hand - to decide how you would do it if you only had paper receipts of what was done. Because IF you can define how you would do this on paper, THEN you would be able to do it by computer. If you CAN'T define the process-by-hand rules, you can't do this at all.