First off you need to see what zone your hunting. You can see that here.
http://www.iowadnr.com/wildlife/files/deer_nrzones.html

Once you find that out you can check the 2006 application information here. This will give you a idea how many people applied for your area last year and how many didnt get a tag. Keep in mind people can apply for points only now then when they want to they can apply for a zone. Also some people may not apply for the same zone every year. This will give you a rough idea.
http://www.iowadnr.com/wildlife/pdfs/06nrdeer.pdf

Applying with a landowner doesnt get you anything. They have to apply just like you and I for a license in the draw. If they do not get pulled for a tag they then can apply for a antlerless only tag for their property. You can read that here.
http://www.iowadnr.com/wildlife/pdfs/06nraffidavit.pdf