I'm running 3 OS X (see my signature

), including Mavericks and the default Lion OS. I had problems with Mavericks which was part of the reason of me downgrading to Lion, but then what I had was a stock mechanical HDD and the miserable 4 GB of RAM in a
PRO Apple laptop bought for around €1.5K (they could've put at least 8GB RAM and 250GB SSD for the price and the class - it wasn't MacBookAir after all but the latter had better components!). I was exclusively on Lion for almost 4 years and get back to Mavericks a month ago when I maxed out my MBP with SSD and RAM. I have to say that starting with Lion the OS X certainly became more power and speed hungry so even in 2011 a spinning drive and 4GB RAM displayed major issues. I run Mavericks and High Sierra from an external bootable SSD through USB 3.0 interface with Lion taking up the internal SSD and have to say with upgraded hardware internals it now runs a LOT better than it used to 4 years ago.
The main problem with older version is actually not so dramatic as many feel the need to stress it. And no, it's not security either: I browsed the darkest corners of Internet with Safari 5 in 2015-2018 yy and had not encountered a singled threat or a breach. A thing that hit me most wasn't security but compatibility since many sites would simply either refuse to load or crash Safari (it seems majority of web-sites with all their fancy "fluid" animations are being built only as the mean to push more ads and track their visitors: being reduced to only
useful core any browser would be capable of navigating them smoothly), I had to download Waterfox and Chrome which I dislike - I'd rather be running Safari but I have no choice. I use it only on light-weght sites.
In addition sharing functionality suffered to the level of becoming totally unusable - Google Maps, Facebook and Flickr in Apple apps (former iLife and QuickTime Player).
However, since working experience doesn't boil down only to Internet browsing or social involvement
every mac OS X is totally usable and lets you be fully productive and creative. I don't use iMovie 10 much, for that I work in Lion in iMovie 9. Most of my apps are in Lion only and some much needed and frequently required - in Mavericks and High Sierra. 3/4 of my working time I spend in Lion (50%) and Mavericks (40%) with only 10% going to HS (you wouldn't believe what for - Twitterrific

)
All said above applied to Mavericks. I re-examined it and found many features Lion lacked perfectly neat and welcome. I'm not satisfied with everything, I miss some small but practical perks I'd gotten used to in Lion. But I like that even in 2019 I can run more compatible apps in Mavericks that simply wouldn't run in Lion and for which I had struggled painfully to find viable alternatives.
No need to ugrade annually - they support every OS for 3 years since the release date and even then it's OK to continue using. Those who work in corporate Mac-environment - I don't envy you.