Although I’m late to this thread (been traveling for work), I found it interesting and amusing for myself to try to put down my “rules” in anything approaching a succinct form. And I failed entirely at the succinct, but here they are anyway...
The first rule is easy – the “new” print price is irrelevant. With few exceptions (textbooks or other books with graphs, diagrams, pictures, equations, etc.), I haven’t bought a new DTB in years. Like some others in this thread, I don’t even look at that price.
The rest of it gets harder and goes by type of purchase
Case 1: If I’m buying it to format-shift – to replace a DTB I have sitting on my overstuffed shelves, it has to be really really cheap, like $0.99 or $1.99, maybe $2.99 in very rare cases. And I feel no guilt for wanting/waiting for such a low price because the author has already gotten paid the standard one-time for the physical copy, whether I paid them myself buying it new, or they got paid by someone else if I bought it at a used bookstore. (Yes, I appreciate that there is some sort of “loss” to the author if I bought at a used bookstore, but only if I would have paid new price otherwise, which was almost never the case for the impulse and/or very old/OOP purchases I tended to make at used bookstores.)
So in my case, the author/publisher lose the opportunity to get a second, although smaller, purchase from me. From their viewpoint, hopefully they are at the right point on the demand curve to get purchases from enough other folks who either have never read their books, or are willing to pay more than I am to replace DTB, to make up for foregoing a second purchase from me. But I sometimes wonder, given that I am someone who is already proven to like the book, and given that I've been known to buy entire backlist series at $0.99 each - such as Amazon's years-ago one-day $0.99 sale on Ed McBain's 87th Precinct titles...
As an aside, I think one of the better models I’ve seen for trying to create some price differentiation on older series, to extract maximum value both from folks like me and from folks who will pay more (and perhaps aren’t as assiduous about watching ebook prices), is the idea of brief rotating price drops on all the titles in an older series, rather than just the first one. Archer Mayor has done this, the US versions of Margery Allingham also come to mind, many Endeavour Press series do this, and also, recently, Open Road seems to be playing some with this model.
Finally, if the price looks like it is never ever going to be something I consider reasonable, and if at some point I really want to reread a book, I will just sacrifice my DTB copy and get it scanned for a couple of bucks instead. Although I’m not a big fan of reading PDFs, I am okay enough with it to do it from time to time.
Case 2: If it’s a new-ish fiction title that I don’t have, and if it’s available in ebook at any of the three libraries I belong to, I’ll check it out there, and then wait for it to come down to maybe $3.99 or $4.99 or so, if I liked it and still want to buy it. (And since many never come down to that price, I often end up not buying…) If it’s not available at a library, I’ll wait until it comes down to a typical mass-market paperback price, and then buy it, but I’m a lot pickier in that case. (And again, since many never come down to that price, I don’t end up buying…) Like someone else said upthread, that’s pretty consistent with the way I was before e-books – I never bought hardcovers, always either waited for the paperback or checked out the hardcover from the library.
Case 3: If it’s a new-ish non-fiction title, which seem to skew higher in price, I use the same strategy, but with somewhat higher price points.
Whew! I think that’s it. But, there is a final rule

- for a small number of authors (about 10), none of these rules apply, and I just buy the ebook when a new title comes out!