Life lessons from pondering a lawn mower old enough to vote

When I was a kid, my parents had a yard. I think I was bored and asked Mom for something to do. She said now the grass. Gas lawn mower didn't work, so I use the manual push mower we had. It was dreadful.

We got a new mower. I think I used it a lot for my parents' lawn. I don't think my dad ever mowed. Mom mowed.

I went to college and didn't have a yard.

Didn't mow grass for years, but had a class where an instructor gave the analogy of Michael Jordan enjoying mowing his own lawn but how it costs him more money to mow it than having someone else do it.

It's the same analogy of Bill Gates not wasting time to pick up a $100 bill from the ground.

When we bought a house, a family member gave us a spare mower. A grandma remarried and her new husband Fred unloaded his house and everything he didn't need in it. It was a  name brand lawn boy.

It used to be self propelled, but that no long worked. It mowed but needed strength to push it since the wheels were meant to run on power. It worked 1 season, so I dumped it and got a Toro 3 in 1 self propelled big rear wheeled walk behind mower from Home Depot for $299 in 2005.

I still have the mower. I don't use the self propelled feature since the front wheels are bald and don't have traction when the spin. It's had 3 or 4 rear wheel break. The rope to the ignition broke at start of this season and I messed up the recoil spring putting it back on so I bought a new one off Amazon that didn't quite fit and doesn't quite work without tinkering.

I've been thinking about replacing the mower a few years, but now I'm dejected at spending more than $299 to replace it, though inflation calculator says $299 in '05 is $483.49 in today's dollars.

Will the next mower last 20+ years of functional use?

How long do I plan to mow my own grass? I have moments when I think of getting a riding mower, but the yard isn't big enough or have an even terrain that makes sense for the luxury. I really don't hate mowing my grass since it gives me a reason to be active, yet will I be like my weirdo neighbors and mowing every few days when I'm old enough to be retired? 

When my mom's parents moved to Florida, my Grandpa used to mow lawns for extra money. My understanding is he retired too young and needed the money. My dad said something about him going out with a case of beer on his riding mower ad being gone all day. 

My dad never mowed our lawn as far as I can remember, so I guess it was a putdown since Grandpa hated him.  

Grandpa was pretty healthy when I saw last him (67) in '96.  I think Grandpa had a stroke while walking and broke his neck on his 69th or 70th birthday. He was quadriplegic until he died at 72.

I never visited my grandparents in Florida until after Grandpa had been gone 23 years. Grandma was always sharp though she was in her 90s but she seemed to be losing her mind and passed away a couple months after I visited her.

My mom lives in a condo and hasn't worried about mowing since she was 62 when my dad was still alive.

I guess we could go the condo route by the time the next mower needs replaced, but mom seems annoyed by her HOA whenever it is a subject of conversation.