Any retirement spending regrets?

[fpuhan]

I'm only six months into retirement, having delayed doing so for seven years after becoming eligible. So, it's too early to regret any spending.

Before I pulled the trigger, I bought and paid for a couple of travel trips. I went to Peru in November and just returned from a month in New Zealand and Australia (where I very nearly bought a Maton 808TE, but I couldn't see schlepping it around with me, and shipping costs to the USA would have been prohibitive). Both I had paid off before retirement kicked in, so now I'm beginning to watch my bank account.

For the time being, I have enough in my checking account to last me for a bit while my three retirement accounts continue to accrue (I hope). I carry no credit card debt. I bought an inexpensive new car with a 10-year/100,000 mile warranty, so I'm hoping car repairs won't bite me. My biggest concern is taxes, but even if I regret paying them, I can't avoid doing so!

My incredibly smart and experienced mentor (rest his soul), once tole me, "If you're not having fun, you're not doing it right." It's hard not to keep an eye on my finances, but I'm not going to allow worry and concern diminish the quality of my life. After all, isn't retirement about enjoying the fruits of your labors?

[Matthew Sarad]

Not really.
We bought a rental in the local mountains after getting Solar panels on our house. Put the new roof, updated plumbing and electrical on our home before retirement. AC and Solar after retirement.
I went from $100k in the bank to $20k.
The Rental needed a new roof on the dwelling and storage shed. Now the monthly rent is paying back.
As a retired teacher, I saved wisely.
That $20k is the Deferred Maintenance Fund.
I'm 68. The AC and Solar should outlive me.

[LAPlayer]

Originally Posted by Matthew Sarad

.....We bought a rental in the local mountains after getting Solar panels on our house. Put the new roof, updated plumbing and electrical on our home before retirement. AC and Solar after retirement....

My dad was an investor and told me while still in college, "buy all the real estate you can afford, as soon as you can afford it". We scrimped by on tight budgets for many years because, like other businesses, the music industry can be boom-to-bust in short order. However, it is worth it today. Income from paid-off rentals, while your principal is still appreciating, is golden.

[Mr. Jelly]

I ran into an intelligent hard working nice guy that worked where I had. He's always been an open person and he told me about his wife's past and present health issues and his son having died from health issues. I explained that my wife and I were moving into a retirement community. At which point he told me that he is broke. I asked about his 401k. He then told me that he gambled it away. I was shocked as this person was never the type to do these types of things. He was always levelheaded. He had to of urinated away $500,000 to 1M easy. Now he is dealing cards at the casino at 70 yo because he has to work to survive.

[Matthew Sarad]

My friend of 50 years, a fine drummer and singer is going through very hard times. I found him a $625 a month rent in a double wide mobile home in a local mountain community. When I found out it was for sale and my friend would get evicted and become homeless because hi SS check couldn't afford a higher rent,I bought the property. At 68, he drives for Uber Eats, making from 0 to 25 dollars a day. His identity was recently stolen, his psychiatrist's office hit him with a $150 co pay and he is $65 in the hole.
I gave him $250 to get through the month until his next SS payment comes in.
He's miserable.