2. The costs just really add up even when when flying bare bones. I could take a Sat afternoon to go have lunch at an airport 60 miles away, for $450. I could probably drive there in the same amount of time. For a longer distance trip the plane might be faster but unless I just fly there and back the owner is going to want to be compensated for the time it is sitting on the ground while his fixed costs accrue.
Generally renting an airplane is done by "Hobbes Time"--basically the amount of time the airplane is running, not when it's just sitting on the ground. That means that 4 hour lunch to an airport 60 miles away in an airplane that rents for $110/hour does not cost $440. It costs more like $150, assuming about 0.7 hours each way. (Some rental companies charge a minimum Hobbes time for overnight stays; one club I belonged to charged a minimum 2 hour/day charge for overnight stays; if you fly less than 2 hours that day they rounded up to 2 hours.)
3. The regulatory atmosphere makes just about any kind of modern technology incredibly expensive. We're talking $1k for a radio, or $10k for a GPS that might have looked modern in the mid-90s (oh, and $3k/yr database updates). You can get modern glass cockpits but that costs more than the 40 year old plane that you want to install it into. Some of these devices can be bought at 1/10th the cost minus their certification, so that they can only be legally used in an experimental plane (despite being identical hardware).
It's extremely common to see pilots use the old ILS/VOR receivers in their airplane coupled with software like ForeFlight for the iPad. The ForeFlight subscription is cheap--perhaps $150/year for geo-referenced IFR charts and geo-referenced taxi-way charts as well as updated VFR maps. That's how I got my instrument ticket, by the way: steam gauges and ForeFlight on my iPad. (ForeFlight for situational awareness, and the steam gauges to make it all legal.)
5. Honestly, the flying community really comes across to me as curmudgeony. Everybody wants to do everything the way it was done 50 years ago. Things like fuel injection, engine computers, automatic fuel mixture, and automatic transmissions are considered scary new experimental technologies. We fly around in planes with float carburetors which can ice up on humid days. Costs certainly interfere with modernization, but so does the culture.
It comes across as curmudgeony because there are a lot of curmudgeons who are attracted to the field, and who are spending every spare dime they can find on their love of flying. And once you get your ticket who can resist the challenge of going up in an old biplane, just for the heck of it?
That said, I agree that part of the problem is regulations: taking a car engine (which can easily operate at 10,000') and putting it into an airplane is damned near impossible without years of regulatory work--and why do that when a Lycoming based on 1930's technology is already certified by the FAA? And don't get me started on glass panels costing $20,000 when a handheld (with similar features) cost under $1000 but can't be legally used to shoot an IFR approach.
Then for me personally I really struggled to deal with moving air. I really had no trouble with the concepts, but it felt like I was swimming in a rip tide half the time I was in the air, constantly being bumped about by erratic currents and having to adjust. Sure, I could land the thing, but I was never really quite sure when taking off if my next flight would be my last. My instructor would tell me that I was doing everything just fine, but it felt like skillfully driving down the middle of a freeway coated in ice; perhaps some would fine this exhilarating, but for me it was bordering on terrifying.
See, for me, I found that a lot of fun, once I got over my air sickness. Unlike some pilots I love doing pattern work, because I love the challenge of landing the airplane, and trying to finesse each landing to make it into 'greaser' (where you only hear the wheels touch down, you don't feel it). I could go out right now and do pattern work all day and be extremely happy.
But that's a personal thing--and if this ain't your thing, it ain't your thing. Like people who don't like building computers from scratch (like me)--if you don't like doing it, then don't.