Five Years of Plane Ownership: The Best Decision I Made During the Worst Year of My Life

In December 2020, I flew to San Francisco to buy a multi-engine aircraft I wasn’t qualified to fly.

Less than a year earlier, I’d been divorced. We’d sold our marital home. I was living in a small apartment, trying to figure out what my life looked like now—suddenly free (and burdened) to make decisions by myself for the first time in 15 years.

The plan came together quickly. Maybe too quickly, if you listened to the rational voices around me.

Why a Plane? Why Now?

I had recently earned my private pilot license—a hobby that forced me to leave the house and concentrate on something external while dealing with the trauma of my life, compounded by the height of COVID lockdowns.

I’d trained with Nassau Flyers at KFRG in a Cirrus SR20, which was a fantastic aircraft. But I was frustrated with renting afterward. It was difficult to take a plane out for a whole day, let alone overnight. And I wanted more.

Unlike my other hobbies, when I was flying, it required 100% concentration. There was no room in my head for worries or stresses about home life, work, or anything else besides what was happening at that moment. In the cockpit, the chaos went quiet.

I don’t know if what I needed was escape, freedom, or control. All I know is that it worked.

The Choice: DA-62 vs. SR22

My choices came down to the Diamond DA-62 or a Cirrus SR22. Both are beautiful, modern GA aircraft—sexy, aspirational goals for any newly minted pilot.

Ultimately, I went for the DA-62 because I wanted the extra passenger capacity: seven seats versus five. I had two young children, and I wanted to leave open what the future would hold—room for any hypothetical future partner I found, and a theoretical blended family unit.

At the time, I had no idea how prophetic that choice would be.

The tax incentives in 2020 also made this financially more viable than I’d expected. I had been in touch with John Armstrong, the owner of Lifestyle Aviation, who I ultimately bought my plane through. When I told him my plan to purchase an aircraft—and the context of what was going on in my life—I’m pretty sure he thought I was crazy.

But John talked me through the process calmly and rationally, with eyes wide open to the reality of aircraft ownership. I’m thankful for his friendship and guidance at what was a difficult time for me. We remain friends today.

John had been hunting for the perfect plane for me. He tracked down N520RA: a Diamond DA-62 owned by an aspiring pilot and Silicon Valley entrepreneur whose ambition to fly never caught up to his free time.

I hoped this wasn’t a forewarning for me.

(It wasn’t.)

San Francisco: December 2020

At the time of purchase, I had my private pilot license and a high-performance endorsement. I didn’t have my multi-engine rating—which is, obviously, an FAA requirement for the Diamond—or my instrument rating, which was an insurance requirement.

So I hired a professional pilot to fly it back with me. My plan was to train in my own aircraft once I got it back to New York, and the insurance company made an exception for that.

Technically, the purchase wasn’t final until I arrived at the airfield in San Francisco and called the escrow agent to release the funds upon inspecting the plane. It was surprisingly anti-climactic. The seller and the brokers weren’t present, so it was just me, the pilot I hired, and the front desk agent at the FBO who had the keys and was waiting for permission to hand them over.

I don’t remember anything particularly emotional about the signing.

But we took off immediately afterward, did a lap around Alcatraz, and then buzzed over Half Dome in the Sierra Mountains on our way out of California.

I knew right away I had made a good decision.

Four Months of Training

It took me four months to get both my multi-engine and instrument ratings, and I did it all in my own plane. It was a great experience. By the time I first flew N520RA alone, I knew that aircraft backwards and forwards.

The insurance exception to train in my own plane was critical. I landed at KFRG with an aircraft I legally couldn’t fly solo. But with a competent CFI in the right seat, I learned the systems, the procedures, the quirks—all in the plane I’d own for years to come.

That first solo flight—the moment I finally took N520RA up alone—is a memory I’ll never forget.

The Lease Decision

I made the decision to dry lease the DA-62 almost immediately.

A plane mostly sits on the tarmac, collecting dust and draining your wallet. It’s better for both the aircraft and the owner if it gets in the air more often. I lucked out and had some great lessees over the intervening years. Each person had their own draw to aviation and different life phases that brought them to this very capable plane.

I’ve always been entrepreneurial, and making this plane into a business felt like a very natural synergy for me.

At first, I was nervous about other people flying my plane. But there were a few competent instructors at my local airfield who helped with transition training, and I got to know the lessees very well. I came to trust in their piloting ability—and in the process, I built a small aviation business around an asset I loved.

Five Years Later

It’s hard to imagine what life was like without the ability to hop in my plane and be 200 miles away in an hour.

In the 1950s, they thought that in the future every family would have a plane, and flying would be ubiquitous—as common as going out for pizza. That future never materialized for most people.

But I feel like I’ve been living there since 2020.

My kids are now entering college. And I have two more—just babies, ages one and two—with the blended family I had planned for. That hypothetical future I was designing the cabin for? It’s real now. It’s here.

I’ve flown as far west as California, north to Montreal, and south to Puerto Rico. I spent one New Year’s Eve on Long Island, Bahamas—about as remote a place on earth as you can reasonably get, and only accessible if you have your own plane or boat.

I regularly have experiences that I don’t even know how to describe to people who don’t have aviation in their lives.

It’s been one of the best decisions I’ve ever made.

The Pattern Continues

I did find that my trips were getting longer and longer. So I recently bought a single-engine turboprop with a partner—a plane I also wasn’t qualified to fly when I got it.

But that’s an adventure for a different day.

If you’re considering aircraft ownership—especially during a chaotic chapter of your life—here’s what I’d tell you:

Don’t let perfect timing stop you. There’s never a “right” moment to make a big decision. The plane didn’t solve my problems, but it gave me something I desperately needed: focus, freedom, and a reason to look forward.

Build the life you want, not the one you think you’re supposed to have. I bought seven seats for a family that didn’t exist yet. Five years later, I’m buckling those seats every weekend.

Get good guidance. John Armstrong didn’t just sell me a plane—he walked me through one of the hardest decisions I’ve ever made. Find people who will tell you the truth, not just what you want to hear.

And if you’re ready to experience what I’ve been living since 2020, let’s talk. N520RA is available for lease, and I’d love to help someone else discover what’s possible when you have your own wings.

Daniel Eisner is the owner of N520RA, a Diamond DA-62 based at KFRG Republic Airport in New York. When he’s not flying, he’s building businesses, raising four kids, and planning the next adventure.