More definition maybe needed:
-Budget: 50k , 75k, 100k. ?
-Useful Load: 4 people plus fuel: 600lbs passengers, 100lbs luggage, 300lbs fuel?
-Range: 300lbs fuel would get you 3 hours on 12g +or- 4 to 500 miles

Once this is more define, it will narrow your search.

-Grumman's could fit in that thinking. Inexpensive to operate, and good hauler, mine is 985lbs useful.
-182 are great, more weight, same speed, more maintenance cost.
-Bonanza's may be out of reach for now.
-Cherokee six is another one that comes to mind, but fuel burn is high. maintenance can be expensive. Great haulers.

Welcome Amy! Lots of good thoughts here, and you've come to the right place for good advice.

I was in your shoes 8 years ago. I found a great partner, and we bought an A36 and have never looked back. It's amazing how much more plane you can buy when you are paying 1/2 of everything. We even sprung for the 550 upgrade in 2014 (love it for any naysayers), which I would likely not have done by myself.

Partnerships have to be well thought out, and a good partner is the absolute key. That said, if you can find that person, you open a LOT more doors financially. My partner and I have both wanted to use the plane at the same time about once every two years, and we each fly 50-100 hours per year in it.

Just a suggestion to consider!

Much as I love anything that says "Beechcraft" on it, I'm pretty sure a Grumman Tiger will do everything a Sundowner will do, while looking better, handling better, and going faster.

and much easier to find a buyer for when it's time to trade up

Obviously its depends on your budget, but I'm partial to Grumman Tigers and Bonanzas. I instructed in Cheetahs for several years and they are nice but don't like hot/heavy gross weight conditions, The Tiger is a much better plane. Cruises all day long at 139 knots on around 10-10.5 GPH. Very sturdy, easy to work on and cheap to insure. Also surprisingly roomy on inside. I once had a 6'3 guy in the back of my Grumman and he said he had lots of room. I folded down the back seats and camped in mine a few times.

Unless you are going on longer trips (like 1000 miles) I think the Tiger would be a better fit (and they are so maneuverable and fun to fly). I love being able to slide the canopy back on a summer day when taxiing around to stay cool. I owned a Cherokee Six for two years and it was a beast, but thirsty on the fuel and pretty slow.

The Bonanza is obviously a bigger step up, but if you find a good one you will fall in love. Built like a tank and although parts can be expensive (depending on where and how you get them) they don't break very often. Just try to find a plane that has been flying and not a "hangar queen".

Amy - welcome to Beechtalk and good luck with your search!