I'm so glad you wrote about this.
I'm writing a point-solution for my flying club that has absolutely everything you could ever want about a flying club's management.
For those of you who know me, if it's worth doing, it's worth overdoing!
Manage2Soar is what I'm calling it.
My club has all flights and all flight instruction logged for the last 20 years. The software is old and scary and obsolete and needs a total re-write and probably has lots of Little Bobby Tables problems.
So I'm rewriting the whole thing in Python and Django. I'm writing it to be flexible enough for other clubs to use. Since I really don't know how other clubs operate, I'm making a lot of educated guesses. I'd love to interview lots of different clubs to see if they operate so differently that this would be impossible to use. Contact me!
It's got:
Flight Instruction records, flight records, maintenance records, source-of-truth membership management, flight training syllabus, performance charts, daily flight log input software, volunteer duty management, calendar management, blackout-dates management, ad-hoc flight operations management, flight information database for all aircraft and tow planes, you can export flight logs to QuickBooks to make the treasurer's life easier. It's got 61.87 pre-solo compliance checks, 61.109 practical test prerequisite checks, it's got annual inspection tracking, transponder inspection tracking, parachute repack interval packing. The Instructors-only section has a written test bank, and when a student is ready for a written test, the instructor constructs a test from the test bank, the student gets it the next time they log in. There's a lot more than could be described in this without sounding like a sales pitch. (too late!)
It's all open source. It's all on GitHub. It's NOT friendly to install yet, but getting there. Code is pretty well documented. Lots of README.md files, .erd files describing the way the tables relate to each other, pytest smoke tests built-in. I've duplicated my club's legacy database into the new one, and I've entered data by hand for each day's operation. So far, so good!
It's a labor of love, a work in progress, I'm a few months away from a demo-able solution. You can see my code commits have tapered off...
I've been in contact with several clubs who would love to have this to help them get out of the age of paper logs, and submitting lipstick-stained cocktail napkins to the treasurer for billing.
I can send you a Google Docs document describing all the features if you're interested. I won't post it to rasprime because I haven't yet redacted the personal information from the screenshots I've made of the dev system in that document.
Here's a few screenshots of the dev system:
Analytics of all the flights we've done. 20 years worth of stats, but this page just shows the trends from 2011 to 2025. 2025 has been a super sucky year for us!
Each flight operation is kept in the database, and once finalized, can't be modified without a superuser unlocking it. Anybody in the club can pull up the flight logs to see who flew on what day. Or if you forgot to get the times from the duty officer, you can log into the system and get your times here.
The duty officer logs all of the flights in our club. We stopped using paper in 2003. We had to computerize everything because we pissed off several treasurers in a row because of illegible log sheets. Word of advice: Keep your tow pilots happy and keep your treasurer happy!
You can fill in this flight log with a smart phone or a dedicated laptop at the field (which we have for our club). The system knows what gliders are single seaters or double seaters, doesn't allow you to select an instructor or a passenger if it's a single seater. Launch time and landing time have a "now" button so you don't have to look at your watch.

How many students do we have? LOTS! How are they doing? Eh. We've got a progress bar for how they're doing for 61.87 signoffs, and 61.107 training. The instructors can see at a glance how everything looks for any student. Our club shares students among instructors, which has positives and negatives. The only way you can share students among instructors is if there's a good repository of documentation for the student's progress, and the instructors have to agree to a syllabus. Illegible logbooks with poor penmanship really don't cut the mustard for sharing information about a student's progress. Getting flight instructors to agree on anything is difficult. Instructors are like cats. The more of them you have in one room, the more mayhem. Instructors do what they want, they lick themselves in front of company, etc. I think the biggest achievement was getting them to all agree to use the syllabus and use the system. Any obstinate instructors who didn't want to participate got to be duty officers or got to push gliders around.

We've been using a pretty good training syllabus for the last 20 years. It's got lesson plans suited to our needs, and lesson plans that remind students what the standards are.
All of the syllabus items have a page dedicated to describing what's expected. The content is editable by the club's instructors.
In the case below, this is the "needs for checkride" page. This dude is post-solo and is working on qualifying for the practical test, and you can see he's still got some items to clean up before the club can present him to me for the practical test.
The software figures out if the candidate has enough flights recently, enough flights total down at the bottom.
Since everything is in the database, we can reconstruct your logbooks if the dog ate them. Here's my logbook, which is just at the club since 2005, when we started logging everything to the database: Click on the magnifying glass to get all the information about this flight. All dates are listed in the ONE. TRUE. DATE. FORMAT: ISO8601. If you're a passenger and not PIC, it still shows up in your logbook anyway. The times don't go toward the totals, and are listed in square brackets.
Hey I see a bug: I have some flights listed as "Solo" but a passenger is listed. I guess I'll have to fix that tomorrow. (issue logged)
Flights where you had an instructor fill in an instruction report have the relevant syllabus sections listed, followed by the instructor's signature. Details about what was accomplished and to what level, followed by a short (or long) rich-text essay from the instructor. You can see this by clicking the magnifying glass next to the instructor for your flight, or you can view your instruction report record.
I'm still having fun writing new features, but will eventually get around to doing the less fun work of writing the ansible playbooks to build a working system. I'd love to have some beta testers to see how this works for your club. I really need to know some meta-information about how clubs operate so I can make this less of a Skyline Soaring point-solution, and more of a piece of software that will work for other clubs.