Student pilot checking in. My situation is that I've got access to a Cessna 182 until the end of the year, at which point I should probably buy my own airplane if I don't want to be a leech.
Comments the others have made are relevant: how far will you be flying, with how many folks? The answers to that help determine which aircraft works well for you. In my case there will be some monthly 550 mile commutes, but most of the time I'll be flying with a maximum of two people, and can probably borrow my friend's C182 when I need more capability (we'll probably trade planes that week.)
So, planes to look at as I see it are as follows.
Please note that I've never owned a plane, and there may be some significant issues to take into account that I'm simply ignorant of.
- Mooneys are cool. These are reasonably fast and efficient, but they're not known for their comfort. My wife has back issues, so I ruled this one out, but it deserves significant consideration.
- The Cessna 182 is the "do everything acceptably" plane. Buy one and you can carry 4 people with bags comfortably, and you've got a plane that's simple, well-understood, and easy to maintain. Other aircraft are faster, more efficient, and so on, but this is probably the baseline that other planes should be compared to. It's just a good, basic, do everything plane.
- The Cherokee series is worth looking at. In my case I'm giving serious consideration to a 180hp version. Not as big as the C182, carries a few hundred pounds less at a slower speed, but it's also cheap to maintain and the trade-off is lower fuel burn, therefore a lower cost per hour to run it.
- The Comanche is an older Piper product, but these are well-loved by their owners and are well respected. Comfortable, available with 4 cylinder (180hp) or 6 cylinder (250/260) Lycoming engines, these look like a plane you can buy once and enjoy forever. It's also on my shortlist.
- The Bonanza and Debonair. Lots of gravity around this line that eventually sucks many pilots in. It's what many aspire to, and are known to be comfortable and fast and well-built. Research is needed here though, as it is with the Comanches.
- Grumman Tiger. This is a fixed gear cruiser that's pretty fast and pretty cheap to run. Lots love them.
- Cessna 177B. Call it a roomier Piper Archer with a high wing. Some love them, some really don't. I've never sat in one so I can't comment.
That's the list of those I'm considering. Cessna made a range of retracts that are interesting, but the possible gear issues made me wary, and my mechanic's unwillingness to annual them ruled them out. If well maintained they're supposed to be pretty reliable, and if the trade-offs are acceptable a 182 or 177 with folding wheels could be really appealing.
In the end you're going to need to define your mission, so you can make an appropriate trade-off between cost to maintain, fuel economy, speed, comfort, and cost. You've got 50 years of planes to choose from as well, so research isn't a bad thing.
If you're like me there are a few planes that will work well, and making the decision about the trade-offs, and then finding the right example to buy is the hard part.