I think my confusion is a result of printing out the Pressed Penny Application and it has a spot for Passenger Name. If I have a passenger along for the entire trip and have them hold the flag (1) in each picture and we're willing to get only one cert will both of our names be listed on the cert? Not trying to be difficult here just want to make sure of what we need before we start.
First off, the IBA flag sold in the store is not the "Pressed Penny Insanity flag", per say, but it is an IBA flag that can be used for this ride. The numbers are random. Most cert rides do not require a flag, only gas receipts. Some specific theme rides require a specific theme flag for that ride, (Gator 1000, only done at an IBA event, for example or the Eggsanity Rides. You would need to buy and use the specific event flag for those types of events). For IBA rides that require a generic IBA flag like this one, yes, the flag from the IBA store is the one you want.
The Pressed Penny Insanity, when correctly finished and submitted, gets you a Certificate of Achievement, not a ride certificate. There is no mileage value for this ride. To a degree, it's on the honor system as to start and finish dates, but you have to collect the 100 pressed pennies, (or more), from the required number of states or provinces, during that one year period that you specify on the application form. You should put the date and location of each pressed penny on the sleeve when you press them. Some riders like to add the odometer reading too.
This is an IBA "ride". Since you must be an IBA member to gain entry into the IBA store where you purchase the flag, I'm going to go out on a limb and suggest you need to be a member to submit for a certificate for doing the pressed penny insanity ride.
If you are an IBA member and you're riding with a passenger, (pillion), that would normally be one entry, one flag and one certificate, with the passenger mentioned on the certificate along with the rider.
If your passenger wants to submit for their own certificate, you would need two flags, and two coins for every location, two sets of documentation for every location, etc. In other words, they need to do all the work too, not just come along with you and submit all your documentation and ask for a second certificate with their name on it. They should be an IBA member if they are submitting for an IBA certificate, but that's my opinion, not clearly stated by an IBA official. Normally the IBA does not accept submissions from non-members, unless they are becoming a member by riding one of the entry level rides. Since the PPI ride does not have a mileage figure attached to it, I do not believe it qualifies for earning entry into the Iron butt Association. I could be wrong, as the National Parks rides have apparently been used for the first IBA ride and those do not have a minimum mileage associated with them either. Seek Clarification on this if you wish to attempt to gain membership by submitting this ride.
Note: A US penny is 0.75" in diameter. Most pressing machines elongate the penny, not really making it any wider in one direction, but thinner and longer in the other direction as it's elongated. Expect them to vary, but generally be around 1.25" to 1.5" on the long side. The Amazon link in the IBA Pressed Penny Insanity is to 2" x 2" cardboard coin holders in small dollar size. These are likely too small, since the modern golden dollar coin is only 1.043" in diameter. I would suggest that anyone wanting to use coin holders like this order the "Large Dollar" size. A large US dollar coin is 1.5" and likely what is shown in the pictures on the IBA web page. LINK
You can buy pressed penny holders too. I found some on ebay HERE "Elongated Cents Oblong 2x2 Cardboard Mylar Flips Pressed Penny 100 Coin Holders: for $8.
And I've seen wallet like holders for collections as well. They usually only hold 32-50 pennies and leave very little room for putting date/location/odo on them, even with a label maker set to small font size.