Using ZC 1.3.8

This questions started out about attributes, but a little history as you may suggest that I am barking up the wrong tree here . . . I have a single product (site not live, sorry) where I am selling to one person, who may or may not be the actual "user" of the product. So, in other words, mum is buying this product for her son, her daughter, and perhaps herself.

Here is how I envisioned it, but perhaps there is a smarter way .

. . "Product A" requires Participant Name, Participant DOB, Participant's Education Years Completed, etc.

"Product B" is identical to "Product A" (remember I have a single product), except that the price is discounted -- it requires the same demographic detail for EACH "B" ordered.

Back to the attributes:
I created Option Names, and then Option Values for those names, and then attempted to place these attributes on one of the products. Name (which is text) and e-mail (also text) work just fine. However Gender, which is a dropdown asking for "Male" of "Female" gives me the following error:

"Attribute Option and Option Value Do NOT Match - Attribute was not added - Participant's Gender : TEXT"

Similar attribute not added problems happen for one of my checkbox choices (I want to user to be able to tick all that apply for that particular participant).

What I am doing wrong????

Assuming that is easily fixable, my biggest fear that I'm going to get to a problem when I get to the "Product B" attributes . . .

I don't ever want a buyer to be able to buy more than one Product B, with the same attributes. I'm not talking about a validation here. I just don't want the customer to be asked ONCE for Participant's Name, dob, etc, even though they have ordered more than one of this item. How can I insure that EACH product ordered requires its own completed attributes? -- For now, I am not worried about the customer who purchases two items and enters the same data for both . . . I'll deal with those outside of Zen Cart.

I apologise for the length of this post, but I suppose I would ideally like this scenario, can I do it with Zencart in a more elegant way than the path I've described:

Go to order page and one Product A for $99 is ordered by default, where customer is immediately asked for Participants's Name, Participant's DOB, Participant's Education Years Completed, etc. It then asks, "Is there someone else in your household who might want to take advantage of this Program? Click here if you want to add another participant at $69,"

For this follow on product, customer is then asked for those same demographic items, before being asked again if there is another person at $69? . . . until they finally say, no thanks, that is it for now, and they are sent to the payment page.

Sounds so simple to me, but I just can't seem to get my head around how to best implement it. Your suggestions will be hugely appreciated.

Cheers, Sean