Take my advice with a grain of salt as I am an admitted and unashamed Ruger fan. No Winchesters in the safe at all, never have been.
Regarding Ruger triggers, some are better than others but all are easily improved by yourself or a gunsmith. The .300 Win Mag I got last Christmas had a very acceptable trigger, although I polished it up with a Dremel and a Cratex wheel anyway as I do with all my firearms. Havent replaced any of the triggers in my Rugers, just touched them up.
On the plus side, the Ruger scope mounting system is unequalled for strength IMHO. A mule, two logs and two broken ribs made me a believer. One can argue the relative merits of Rugers cast receiver or one-piece bolt, but its difficult to argue with accuracy. Every Ruger I own is a shooter and a keeper. None shoot more than 1 at 100 yards given good loads, and my .22-250 VT has put 4 shots into 0.5 at 200 yards.
With a synthetic stock you may not find it necessary to float the barrel, but every one of my Rugers is floated, as has been every centerfire rifle that has been in my safe its just something I do to prevent shot stringing.
Then there is the matter of looks, which is highly subjective. Personally, I much prefer the Rugers square-ish receiver, but to each their own.
My suggestion is if your Dad likes the Ruger, get it.