Personally I would move up to a 30+', but you may be interested in trailering.
Catalina's are great and you can find them in perfect shape at huge discounts if they are 2 to 10 years old. I suggest a 30' because the amenities change drastically between 25 and 30 as well as the handling. You can accommodate far more guests with much more comfort. Wheel steering is a big plus and a shower is much better than you may think - particularly if you have kids or decide to sleep over much. When you are at anchor or at the dock - remove the wheel and clip it to one of the many convenient quick holders made for them - they even have folding wheels.
Another quick push for a slightly larger boat - when one or two people move to one side on a 25 footer - you know it. When they move to one side on a 30 footer you will probably not know it. If someone needs to konk out, they can hide away from the group and sleep. If the kids need space to get away or the other way around - its there.
You will find - (mark my words) that if you really get into sailing and trailering is not your thing, you will move up to a 30+ footer in the long run).
Outside of the above, Catalina's are no brainers - they are well known, have a very good reputation, they are easy to sell when you want to sell and move up to the next size, and they are relatively less expensive to maintain because you can purchase many of the interior and exterior parts directly from Catalina - things such as the rigging, sails, cushions, etc.
By the way, when you purchase a brand new boat the off-gassing can be very strong. I became sensitized to the fumes and could not actually purchase a new boat if I wanted to.
The economic train wreck hangover we are in offers up a ton of 2-4 year old boats in mint condition and the fumes should be down to just about zero. They will be hitting a bottom in price over the next couple of years but even now the deals are great - be sure to make your offer at a steep discount - at least 20% below asking (don't hate me readers, but I would offer 30-50% less and get it all day long).
New buyers will ask a salesperson what they think of different boats - you will pretty much never hear a bad word about a Catalina or a Beneteau. If you ask the same question about a Hunter, the salesperson will rightfully ask you what year or tell you that it depends on the year you are looking at - pre-1985 would not be a good thing, they were pretty poorly built prior to 1985. Other boats have similiar reputation problems - Morgans were very well made but some models were real dogs (poor sailing vessels) and others were good racers. What I am trying to say is that you will enjoy pretty much any Catalina, particularly in the size range you are talking about, and when you later go to sell it, you will find the process just as easy as the purchase.
Whatever you do, don't buy a one-off or oddball in this size. Stay away from "well built" tanks, they require an eccentric to sell, usually sail poorly and generally have small cockpits and not enough laughter. If and when you sell your boat a good well known brand makes the process easy.
I would take a good look at anything from the early 90s onward. Very little has changed on most of the Catalina's and others with modern designs. The sterns took a big leap in size and comfort and overall it was around the early 90s that many went to the walk-thru transom which is extremely desirable and the double stern-rail seats are the bee's knees.
Beneteau's are great boats but I do not know much about the smaller sizes.
Beautiful lines, modern designs and good sailors.
From the sound of your plea it is obvious you are leaning to the new side of boats and I think the new designs are miles ahead of the old designs. If the reputation for a boat is that of a tank - just pass it by - unless you are driven by fear.
Spending a pile on a 25 footer makes no sense at all - Buying slightly used makes a ton of sense.
I have never met even one person that has purchased a new boat that did not have more problems with the factory and de-bugging than someone that found a good almost new boat. This is probably not as big a factor in a smaller boat, but it is interesting to note.
I have never lost a dime on all the boats I have owned. Every boat that I owned sold for well above my purchase price to the first 3 people that looked at them and in all cases I owned a boat that was a well known brand with good sailing characteristics.
Take advantage of the great deals out there and buy great wine with the savings!
I hope this has been helpful.
Fair winds - David
