ElleVancouver

This.  Almost every port has that little hole in the wall place with the cheap $2 beers and such..."Virgin's Haven" in St Thomas was one of those places, and it was right next to the ship when were on Jewel in April '15.  It was too hard to leave that place....

In your case, I would try to estimate how much you would drink on an "on day" and figure how much the cost of those drinks are a la carte and compare to the package.
 
I think you will better off a la carte because if any of those drinking days hits on a port day, you would likely save even more money drinking on shore. 
 
I guess what I am trying to say is you have to sit down and figure out the math of how much you think you would drink and see how close you are to the daily cost of the drink package.

Get the select package for your self(wine and beer) and the premium package for him. If you both really do like your drinks, you will come out ahead at the end even if there are some days you drink very little based on my 8 cruises so far with the drink package.
 
Its so nice not to worry about where your bill is at, try new drinks, if the drink gets warm leave it and get another one.
 
While I am the exception to the rule, I get almost my whole package's value the 1st day on the boat. I am on early, enjoy the sail away party and then hit the various bars and clubs during the evening.
 
I didn't cruise until the drink packages came out as I was an "AI" type of guy and heard horror stories about bar bills more than the cost of the cruise.....

They actually do NOT want you drinking every day.  They hope that you will do exactly what you described above and basically drink every other day.  Pay for every day but use it only every other day !
 
As a general rule of thumb...if you can average 5 - 7 drinks each day over the course of your cruise, you will make out, financially.  Of course, it will also depend on which package you get...but they all seem to work out to the same, general average.  Some people just want the beverage package to relieve themselves of the worry of a monster bar bill at the end of the cruise...and some need to use their OBC for something so the beverage package will do as well as anything else.
 
More and more often I am hearing about the drink "punch cards" that they are experimenting with on various ships.  These cards, typically, will give you 10 drinks for around $75 (plus 18% gratuity), making it work out to $7.50/drink which is a fairly good price considering "full" price for a mixed cocktail is typically $12.  Of course, you will have no way of knowing whether your ship and sailing will offer these punch cards but my recommendation would be to wait until you get onboard to purchase any beverage package.  It isn't going to cost you any more to wait (unless the price goes up for the packages...which JUST happened, so it is unlikely to go up again so soon) and there is a chance that they will be offering some kind of discount/incentive or other option (punch cards, etc.) once you get onboard.