Sounds like an interesting biz idea. I have seen this type of specialty advertising done successfully in other ways...like sports calendars.
Before you decide how much to price your ads, first figure out how much your WEEKLY overhead will be.
1. Printing - you ask how much it would cost to print your booklet...the best thing to do would be to get an estimate from a print shop. Here are some of the questions they will ask you:
# of pages
Black/white or color
# of sides printed
2. Labor - will you be putting the booklet together, or will you hire someone to do it? If you do it yourself, do you have the software and technical expertise necessary? If not, software will be an additional cost. You might consider hiring a graphic designer, or negotiate with the printer to do it.
Also, who will be selling the ad space? Will you do that, or hire someone to do it?
3. Rent - will this be an out-of-home, or will you need to rent an office?
4. Office expenses
5. Distribution - how will you deliver the goods and where will you put them? Front-of-store racks? Small specialty store and shops by the cash register? If you haven't already, put some thought into this. You may need to hire someone to distribute for you, and you may need to manufacture racking system. Are the booklets free, or will you be charging for them?
6. Advertising & Marketing - how are you planning to let people know about your booklet? How are you going to create buzz? This is important for both soliciting ad buys and readers.
Now add all these costs together out what the WEEKLY hard costs will be for you to put together the booklet, market it, and distribute it. Now add what you want to make per week for the booklet (what will your salary be, and don't forget taxes for yourself and any employees you hire).
Divide this figure by the # of ads you plan for each booklet. That should give you a fairly good idea of what you should charge per ad.
After you reach your figure, do some comparison with similar publications to make sure you are on target. You may have adjust your pricing because you want to be competitive.
I would also urge you to think about including some content in your booklet...to make it even more valuable. How about a "how to" run a great garage sale, or something pertaining to the customers you are seeking.
Also, consider value-add for your customers...like putting their ad on a website as well as on the hard pub.
Sorry this is so long...hope it helps!
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All the best,