Welcome! You're not asking a silly question at all. There's nothing we love more than buying stuff with other people's money.
You've also got a bit of a different mission than most, and mission is what is best used to guide you towards the right type of airplane. For many people, the mission is to go places, and you've gotten a lot of answers that aren't great for your particular situation because it seems some people are answering based on that habit rather than your particulars.
It looks to me like you've got the following desires/requirements:
1) Staying relatively local - This is never a "requirement" with any airplane, you can fly an ultralight across the country if you want to, but it does mean you don't need something that covers ground quickly.
2) Fun and easy to fly.
3) Two seats, though more is an option.
4) Modern avionics
5) Insurable at 74
6) Not something you need to build
7) Tricycle landing gear
8) You mentioned bush planes, but that you don't actually want to fly in the bush. I think this is because you're looking for a two-seat fun bird, and bush planes are possibly the most thriving segment.
These requirements can point to a few different possibilities:
1) Cessna 150/152, possibly an Aerobat. You mentioned increasing your skills, and being able to do some loops, rolls, spins, etc is one way of doing that. However, the C152 Aerobat wouldn't be twitchy or hard to fly like many aerobatic planes are (stability is the enemy of maneuverability, after all), and it should meet the requirements of your insurance company as mentioned later in the thread. Still has a yoke instead of a stick, though, and isn't particularly likely to have modern avionics so you might need to do an upgrade if that's a strong desire.
2) Light Sport aircraft (LSA). These are often discounted by the industry because not many people have flown them. There's also, to be honest, some really badly built ones. But there are some that are really fun. I rather enjoyed the Evektor SportStar (I think the US LSA version has been renamed the Harmony more recently). It climbed 1000fpm on its little Rotax engine even with two heavy dudes aboard, it had a great view with the bubble canopy, and it was light on the controls and really fun to fly. I've also heard good things about the Czech Sport Aircraft. Finally, Pipistrel has quite a selection of aircraft and is now owned by Textron so parts shouldn't be too big of an issue (though Textron is not known for cheap parts, Cessna is also a Textron company and it sounds like insurance is OK with that). The SportStar has a stick, and many other LSAs do too - Just look at the pictures of the birds for sale.
3) Diamond DA20. Two seats, fun to fly, great view, stick. FWIW, I have not flown the DA20, but I have flown its 4-seat big brother the DA40 and that is a fantastic airplane. The DA20 isn't great if you're really tall (significantly over 6 feet), but neither is the 150/152. I'm 6'4", that's why I haven't flown the DA20.
What you should NOT do is go out and buy a bigger Cessna (sorry,
@Zeldman). They're great at what they do - Being big, lumbering beasts that haul a lot of crap - But that's not your mission, and they are DEFINITELY not "fun" to fly other than for the capability that they have.
I hope this helps, and I hope that if you call up the insurance guy that these are still mainstream enough for them if you want to have insurance.