Addressing the Envelopes

Today's bridal freakout is brought to you by invitation addresses.

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Seriously, people-this is way more difficult than I expected.  Way more difficult than it should be!!  Dear so-and-so, would you like to come to my wedding?  OK!  Yeah, not so easy.  What if one "so" is in the military and the other is a doctor?  And the female doctor kept her maiden name?  Martha Stewart told me that if they are married doctors with the same last name they should be addressed as "The Doctors Smith."  Seriously?  That doesn't seem right to me.  What about a former politician married to a doctor?  This is an actual scenario for me and Martha didn't really have advice. 

As with anything wedding related, there are a ton of resources out there confuse help you.  I had this Martha Stewart guide pinned for months, thinking I would just go there when the time came and it would answer all my questions.  Not only is it not comprehensive, but I don't necessarily agree with everything (see "The Doctors Smith" above).  She did provide me with information on certain cases where the wife's name should go first, which was interesting and news to me (married couples with different last names, for example).

When Martha (sort of) fails you, who can you turn to?  Google, that's who.  My quick search took me to The Knot's guide for addressing envelopes, which was slightly more helpful.  It has more scenarios than Martha Stewart but it still doesn't have everything I need, although I understand no site probably will.

I am also unsure when to use Mrs. and Ms.  What about a divorcee?  What about a widow?  I usually refer to anyone who has ever been married as "Mrs." but I am pretty confident that isn't correct.  I decided to consult the ultimate expert, Emily Post, and that may have been my best decision yet.  She gives multiple options for each scenario, which kind of makes me feel like I can do what I want (within reason). 

Now for the next challenge - making sure I have all formal names and titles correct.  Should I just outright ask guests if I am unsure?  Is that tacky? 

I plan to send my invitations out in just over a month so I am happy to be starting this sooner rather than later.  I am doing my own calligraphy, which is going to take a lot of time, so I need to get this finalized ASAP.

Am I alone in this battle?  Does anyone have any helpful tips?  Can I just send an Evite?