Not hard at all, assuming your other desired reservation is available. The owner simply goes into the reservation program, clicks on your reservation, chooses 'Modify' then does the search for the reservation you want. If it pops up as available, they click on that, then click on about 2 or 3 more pages as they 'step through' the reservation. And that is it. By modifying a reservation in this way, they will not need to add all the information all over again.
Now, if you want to add other people to your reservation then at one step in there, they will have a chance to list more people and put in their information. That takes a bit more time, but is just the same type of thing they do with the original reservation. They still won't have to re-enter your personal information that they already have.
If you are going to do this, you should go through the Rental board here and find an owner who you can work with and trust. Pick someone with a fair amount of experience, who has done multiple reservations before. I am just saying that because you want someone who cares and who has experience with this. Otherwise you might contact them in 5 months and find that they are no longer interested in helping you very much, because they aren't putting much attention into
DVC or the boards. I'm not saying that WILL happen, but someone who has made multiple reservations in the past, over a moderate period of time will already have demonstrated that they WILL be around and paying attention.
When you are initially setting things up with the owner, you need to let them know up front about your possible plans to change and ask them if they can do that and are willing to do it, if the reservation is available. I only say this because a lot of owners use a contract that, essentially says, No refunds, No Do-Overs. I understand the no refund part, but if they insist that they don't HAVE to modify your reservation then they will point to the contract where it will say this reservation is FINAL.
In my contracts I specify that I don't give refunds (though I am a nice guy and I might under certain conditions) but I also specify that I am quite willing to modify, change, cancel, or move the reservation (with no refunds), so long as they let me know by a certain date (which is usually either a month or so before banking cut off, if the points are bankable, or two or three months before the reservation, so I am not dealing with Holding points). I had one guy recently who initially scheduled for a 2 bedroom at AKL in February next year, but then due to an unexpected health development found that he needed to shift to May next year. This put it across my Use Year line (March Use Year) but, since he gave me plenty of notice, I am able to bank the points he would have used this Use Year, and use them next Use Year. We also made arrangements for the fact that the new reservation took a few more points, since it was in a higher demand period.
Anyway, make sure to find someone who will work with you.
I am not completely sure of the policies of the Rental Brokers, and since there are several of them, their policies probably are varied, however, I do know that at least some of them specify in their contract that they WILL NOT move your reservation (even if it is available). They do this in order to save themselves and their renting owners the extra work, because, frankly, it is about the same amount of work for them as it was for your initial reservation, and they aren't making a lot of money to begin with. But if you go through a commercial broker (such as Davids) make sure to find out their policy and get clear on it before you sign. (I don't know Davids policy on this.)