Gratiam et pacem a Deo! (Or is it only gratiam with you?) Of course you're right that the key is what sounds good, since even today overall literacy rates are in the single digits. And university debates, which seems to be the idea you are trying to evoke, are of course oral disputations first of all.
But to spare the poor PhD students who would have to respond to lxxxxv theses in full scholastic argumentation, let's consider a different approach. Have you thought about taking your theses public?
If so, there are several factors to consider. First, effort. You will need to make several copies by hand. A copy for yourself, a copy to send to the archbishop of Mainz. Your university may also want a copy. Philip Melanchthon further informs me that Wittenberg has several churches with very plain doors that you might wish to consider (or you might not; people are going to make up stories one way or the other, aren't they?) Do you really have time to copy out the full three hundred?
Second, numbering. I know how you feel about the importance of the vernacular. But are you planning to continue the proud tradition of Latin numbering, at least? If so, you'll want to consider whether people might misinterpet "C" theses. We would not want you taken for that damn French copycat.
Third, cost. Movable type permits printers to blanket the streets of German cities with broadsheets and pamphlets, since paper is cheap and we don't have to pay for labor of scribes. But paper and ink are cheap, not free. If you have an eye towards a public, you will want to make sure your text can be printed in broadsheet or pamphlet form, rather than needing to be a full book.
And I guess we started off with oral performance, so we'll end there. Consider whether women in their sewing circles might read your theses aloud (would you tolerate that? or would you only yell at the papists for not tolerating it, all while secretly agreeing?). Do upright German fathers really have time to read 100 theses to their families? Are they not supposed to be at work ethically?
With all of these factors in mind, I do hope you will reconsider your decision to add an extra five theses.