To keep the other two threads focused on their topics, let’s vent and post about our “should have” regrets here. 
I will start… Several years ago, we had the $$ to buy a condo in HI. We did not, because it felt like we were splurging. Saw the condo is back on the market at 2X the price we could have paid for it during the RE bust. Oh well…
My best friend’s grandmother’s tiny two-bedroom house, after Grandma passed away.
It would have been worth three times as much now.
During our honeymoon in Paris, there was an awesome chandelier w gargoyles, in the flea market. Have been thinking of that piece for over 20 years now …
I am a big real estate shopper but not a buyer so I have too many regrets to list. However it’s probably BECAUSE real estate has always been an investment to me as opposed to a splurge I have only pulled the trigger on my own house. Maybe I should treat it as a splurge and dive right in? naaaaaaaah
My biggest regret—not buying a small Antonio Guardi when I was a student in Italy. It was priced at only $400 which was a months stipend for me. I did not need it, I only loved it. Now worth well over $28,000.
How about a bunch of puts on a market index at the beginning of the year, because it was obvious it was going to crash.
A 75 dollar piece of crystal that we found on our honeymoon (on the way to our destination) at an antique place. 75 was a lot back then. A couple days later on the way back home when we decided it was worth it (and still had a bit of money)–it was gone.
It was a good lesson though. I’ve made some good purchases over the years knowing that waiting is not always an option.
Should have splurged $100 for the white horse and carriage to go from the wedding ceremony to the reception 35 years ago. At the time it just seemed like the last straw so we skipped it. But it wasn’t that expensive of a wedding, Mom wouldn’t have blinked an eye at paying for it, and I’ve regretted it ever since.
@Marilyn , that’s mine, too! Either a horse and carriage or a limo… We had this rental car that we thought looked pretty good back then, but it really didn’t.
Although, now I’d have an intimate wedding on a beach, so it’d all be different, anyway…
Well, speaking of weddings: I would have made a much bigger deal over mine. I thought I was an “old” bride so I didn’t want a big whoop-dee-do. I should have.
My son and I have been following “Hamilton” since it was going to be the “Hamilton Mixed Tape”…we knew about it years before most folks. When tickets first went on sale for the Broadway production, I didn’t want to pay for the entire family to go and knew that everyone would be ticked if just Son and I went to NYC. Now, for what I paid for 2 tickets I could have taken the whole family.
I should have splurged to see the Sting and Paul Simon tour when they came around together a couple years ago.
I didn’t want nosebleed for that and the good seats were sooooo expensive. I regretted it the next day.
We rented a little shotgun house and had to move because our landlady wanted to sell it. She would have sold it to us for $70K back in the '90’s and we were just too scared of the home buying process to bite. Arghghghghgh!
We should have paid extra for the ocean view on our honeymoon. The mountain view wasn’t so bad on Maui, but the parking lot view on Oahu left much to be desired.
I should have gone to see Pink Floyd perform “The Wall” at Nassau Coliseum back in the day. They only performed it at two places in the US but I didn’t have my driver’s license yet. :((
Back in the '80s, A little old lady was willing to sell my ex and I a house in an exclusive area right outside of DC, for cheap, but I didn’t want to live there because it was too close to my in-laws. She was giving us a great deal AND that was before the explosion in the real estate market. I’ve never made much on real estate, but I still regret that decision.
Cherry cabinet upgrade in our home when we bought in1996. Also should have put in a pool in the back.
Traveling in Guilin, (southern China) in 1981 people were literally pulling the silver out of the earth where it had been buried during the Cultural Revolution. There was a bracelet made of silver Hong Kong coins with Queen Victoria on them, as well as a silver hair ornament. I was being the cheap traveler, so said no.
The Two Grey Hills Navajo rug brought into the trading post, for $97.00 back in 1983-again, the cheap traveler.
It wasn’t me, but the $20,000.00 house on the Monterey Peninsula my mom almost bought in 1970. She couldn’t come up with the last bit of the down payment.
We should have bought the 1800 square foot house on a cul de sac in Irvine, CA across from a park and a school for $245k in 1996. We offered $240k and the bank said no. (It was a foreclosed property and it didn’t sell for 8 more months after our rejected offer, for $244.9k). I think it’s worth $800k now.
I should have gone to visit my high school friend at her college. It was freshman year and her college was sponsoring a new musician for its fall homecoming. Nah. I’d rather stay on my campus and stupidly gaze at my new crush (who never gazed back). I also thought the roughly $50 the weekend trip would have cost was out of my budget. It was early in the semester and I was cautiously watching my expenses. Alas, I missed out on Bruce Springsteen.