Sorry for your loss. If you get the Shell gas station member card (free at any Shell gas station) you can register for free nationwide roadside assistance. Some auto insurance policies also offer a roadside assistance option for a small extra fee.
You can go on the last day but that is not advisable as if you have an issue you might not have time to get it corrected for them to accept the application. Most offices let you apply 30 days in advance while some others allow 45 days in advance (check with your office you will be using).
You do not pick which office you use. You use the one that services the address you are staying at. If you are in a hotel ask them for a screenshot of the TM30 search showing they registered you.
You can extend a Non-B for marriage. You are just changing the reason for the extension. No reason to change to a Non-O. Non-B and Non-O for marriage have the same identical privileges. I am on a Non-B from 2007 and have extended it for marriage many times. Keep in mind the first time you change the reason for the extension your one year extension starts from the date you apply. The next time you extend the one year will be added to your current extension.