Wobby77

Wobby77,
 
Definitely check when you get onboard.  Just because his favorite drink isn't listed on the drink menus doesn't mean they can't make it or that it's not included in the beverage package.  Now, of course, if it's a particular brand of liquor that he prefers, then he's out of luck.

Remember that you can wait a few days before buying the unlimited packages.  As long as there are at least 4 days left in your cruise, you can purchase the package at any point.

We have booked our First RC cruise and it is a repositioning cruise from Singapore to Perth.  14 nights, but lots of stops.  We enjoy the longer cruises and don't mind that there are more older than younger on them (this was our experience last time, but on a different company).  I think we got a great deal on it at $1200 each + tips as we had to go with my time dining, which is fine by us.  All taken care of then :)

To my recollection, there is no loose tabbaco sold on the ship.

I'm with you, Matt ! There is never a shortage of things to snap up my OBC !
 
One of the discussions on this topic (if it is not this particular one) mentioned that you cannot use your OBC in the casino. That is only partially true. While you cannot take your OBC directly and use it in the casino, you CAN cover casino expenditures with OBC by taking a "cash advance" at the casino. The only problem is, it will cost you a 5% "convenience fee" unless you are a member of Club Royale. So you CAN spend OBC in the casino...with just a little bit of overhead.
 
If you have $100 of OBC and you take a $100 cash advance at the blackjack table, your sea pass card will be charged $105. It will be offset by the $100 OBC and the net charge to your sea pass account is $5....but you have successfully used you OBC and, in fact, now have $100 in your hand (unless you foolishly gambled it away !!!).

If you have OBC to spend and there is no risk of what you're booking selling out, feel free to wait for the ship.  The beverage packages are a great example of something that you can wait to book onboard.
 
Things like shore excursions or specialty dining (at a specific day and time) are something I think you should consider pre-booking.  
 
In my experience, I never have a problem spending my OBC money!  It seems to disappear quite quickly

These are about as regular as any cruise out there. Depending on the cruise length, there may not be opportunities to see and do everything but it will be treated just like any other cruise. Re-positioning cruises can be a lot of fun and a good value!

Cruise fares for transatlantic are a good bargain if you book just after the dates come out.  We were monitoring a  Brilliance Tampa to Harvich, England cruise, and it went up in price one week after by $100 per person.  The rates did nothing but raise in rates after.  Glad we booked it early!..... There was nothing extra during the 13 nights sailings except for some extra dining menu's and many Crown & Anchor members.  Overflow happy hour lounges were provided for members. 
 Some cruisers do nothing but transatlantic sailings each year.
 
As Matt has mentioned, the re-positioning cruises are a lot of fun and are a good value!.... .