Welcome to the party Brother.
Last year my wife said, you are grumpy since you retired, just go buy your damn airplane. Yes Ma'am!
I almost bought a Lancair 4P, had a deal in place, but during pre-inspection found out the airplane spent a few years of "unexplained" and unlogged time in Mexico, the maintenance log books were shit. I am 69% certain that plane was flying drugs into the U.S. and had no idea what shape the wing spars were in. Additionally, the insurance on some of the Lanceairs is outrageous because of their accident rate. I was very enamored with the performance of the Lancairs, especially the 4P, they tend to be sleek machines, fast and economical but most models have a high wing loading requiring some extra attention in the pattern. The insurance on the 4P was triple some of the other airplanes I was looking at and ultimately a big deciding factor.
I ended up buying a Piper Saratoga TC II. I wanted to fly but also wanted a travel machine for the family. The guy that owned it before me dumped about $120K worth of glass into the airplane (see below). I flew steam gauges most of my career and was shocked by the SA the Garmin offers especially when it is integrated with the autopilot. I put about 180 hours on it in the last year. Four trips to DC (In-Laws live there), A few to Miami (my parents live there), and a lot of shorter trips in between. Once at altitude I typically I can lean for 13-16 GPH and see around 145-155 TAS.
I started off using my IPad Pro, but found it too big for the cockpit. There was no place to put it so I kept it between the seats and pulled it out to review. I ended up buying an IPad Air with cell service which is still big but I can mount it with a suction cup. The cockpit of the Saratoga is a bit odd around the windshield/Dash and ideally the IPad Air would be more friendly for space, but we have decided to upgrade to a new airplane and it will accommodate the IPad Air. On trips I can do all mission planning on the IPad and I use it in the airplane with Foreflight running as a back up.
As folks have stated above the Bose A2s are great, pricey but they fit is great and the ANR is superb. I tried a few in-ear options, forget the brand name, but didn't like them.
My wife's college sorority was having a big get together in the Fall so I flew her to Tallahassee. She is a nervous flyer and at one point said, "it would be a lot better if you had a plane with two engines"...Again Yes Ma'am so I started an upgrade search. I looked at a bunch of options and I am signing a contract for a new SR-22 this week. Yes I know single engine but with the CAPS system I think it hits her "safety button" STS.
I'll share my thoughts on the upgrade search and what lead me to the SR-22. We want to travel and we have another couple that usually goes with us. Useful load and range were driving factors.
I was going to buy a Baron G-58. Great airplane, fast, and a fully integrated G1000 system. It also has better takeoff performance than the Cessna's. My home base airfield is only 3700' and while I could safely operate a 310 or some of the other Cessna options, the margin would be much smaller. I knew the cost factor would be higher for maintenance and fuel, but again it was insurance that was double that of the SR-22. It has a great useful load until you start accounting for all the extra gas you have to take. It was also the fastest option, although at double the fuel burn.
I really wanted the Diamond DA-62, in fact, it wins hands down on all the performance, fuel burn, and operating cost factors. Single engine climb is well over 600 FPM, Cruise speed is superb, great useful load, tons of room inside and it sips 11.8 GPH of Jet-A at altitude. It has one major drawback that for me was a show-stopper, it has a HUGE fucking footprint. With a 49'3" wingspan there is only one hangar on my field that it will fit in and that hangar has been rented by a company for 12 years. They are building a bunch of new hangars on my field, but they are all too narrow...I will not leave an airplane that expensive outside. Finding a suitable hangar was going to create an hour plus drive at about triple the hangar rate I pay now.
Previous to this I was not a big Cirrus fan to start with. A great friend and UPT classmate was their chief test pilot and was killed in one. They have come a long way and as I started to look the SR-22 met all of my performance wants. It is FAST for a fixed gear airplane...170 TAS at between 16-17GPH. Faster by far then my Saratoga with a minimal increase in fuel burn. Reasonable insurance (as long as you do the training). Also, depending on configuration, it has the best useful load of any of the other options I looked at. I am getting a new normally aspirated SR-22 G6. Flying in the south I don't need the turbo or icing system (which is very high maintenance by the way). I will still have oxygen if I want to jump up to 16K and grab a tail wind. Dropping the turbo and FIKI icing system bumps my useful load to 1269 pounds. I will be able to easily take my wife and our friends, all their bags and almost a full bag of gas which lets us range Charleston, Key West, Charlotte, DC, Nashville, Dallas non-stop.
One other thought in my long rambling post, airplane prices are high right now because of USERRA. If you purchased an airplane by the end of 2020 you could use it as part of a business and go back five years of offset profit on your taxes. Baron Prices are very high, same with the SR-22. I was looking at a 2018 SR-22 G6 and when compared to a new one I can get a new SR-22 for about $60K more, but it will be in my color scheme, have zero time and Cirrus is throwing in a five year tip to tip warranty.
Good luck brother and hope to see you out there.