Burn it all down

He said property tax to me. Said it was 10 years overdue probably 12 now. Perhaps the property is such a disaster the municipality doesn’t believe it would sell?

No, his income tax. Property tax is a secured debt if you do t pay it. The municipality puts a lean on your property. And now municipalities are selling these debts off to bottom feeders who can just foreclose on your property. Those taxes will be paid. One way or another.

In my case, due to my planning it's not like we're going without in the meantime. The ideal is to spend your money when you can most enjoy it. We are already doing that. Some amount of this is also due to medical costs, like when you factor in that I will wind up paying at least $12K (or more) for health insurance guaranteed, with no guarantee that investing the cash I have can make up that difference.

There are likely many ways to skin this cat and all of them are a gamble one way or another.

Ok, you answered the question. The way you phrased the original statement, to my understanding.... Was directed at income not taxes.

I have nothing to add to your current topic.

Mickey and his property taxes?

It was kind of a rhetorical question and perhaps fodder for a different forum topic, though I'm sure there are plenty that would want to burn down at least our tax system as it exists today.

Someone else mentioned that you really don't want to penalize someone for being successful, but the result of that is that as a % of income, poorer people can wind up paying a much higher % of their income in taxes. These same poorer people are in a worse position to be able to do that vs someone considered to be rich. Is that fair?

Yeah, I know nobody said life is fair, but....

"Let's maybe not give tax cheats any more ideas. ;)"

Yeah, cheaters gonna cheat in ways I couldn't even dream of. I tried to enlighten the most vocal SLS tax cheat as to the errors of his logic. Including the "FACTS" about taxes that his very reliable sources gave him. He posted links to the people proclaiming the "FACTS"- many of whom have been convicted of tax issues.

I wonder whatever happened after he told the judge he wasn't going to pay when a court ordered him to pay his taxes. He sure seemed proud of his defiance toward the court...

"Part of this is because my SS benefit will be 16% more for the rest of our lives by waiting 2 years before I pull it. The other is that I have to buy ACA insurance for the Mrs, and the cost of that is income based."

You might want to consider doing an analysis of waiting to file for SS. It can take a long time to recoup the difference of 2 years of not collecting now. 15 years isn't unrealistic. and shit happens- you could encounter one of life's little unforeseen curves that eat your 2 years' worth of savings in a heartbeat.

YMMV

@mayhem, good for you. As long as it legal, I'm all for it.

From mayhem:."At some point, how much is too much, and who gets to decide that?"

I'm not going to put words in your mouth. I'm not going to make assumptions. I'm going to politely ask for you to expand on that statement.

"Some may see this as gaming the system, but it is only using these services to our full advantage."

It can be both. It's neither illegal nor immoral to take advantage of legitimate ways to decrease your tax burden.

I will not be paying taxes this year or next. I saved enough money to live off of for 2 years. Part of this is because my SS benefit will be 16% more for the rest of our lives by waiting 2 years before I pull it. The other is that I have to buy ACA insurance for the Mrs, and the cost of that is income based.

My wife turned 62 so I had her pull her SS, which is minimal. Between that and my one months worth of income (retired end of Jan), our income will be ~$23K this year. My deductions add up to $39+K for 2026, so I will take the difference from a traditional IRA ($39k - $23K = $16K) and move it into a Roth. This is a taxable event, but the added income brings me to the top of the $0 tax bracket.

The following year I will do the same, but it will wind up being a ~$29k Roth conversion as it will only be my wife's SS as income. By doing this, we can more or less live like we have been and only pay ~$225/month for a BCBS Silver plan for the Mrs for those 2 years. If I pulled my SS, her ACA insurance would have been $500-$600 more per month and my SS benefit would be less for the rest of my life.

Some may see this as gaming the system, but it is only using these services to our full advantage. The 1%'ers and I are doing something similar in theory, but I'm small potatoes compared to the income of a 1%er. I have enough for us to live comfortably. A 1%er has enough for a village of people to live comfortably. At some point, how much is too much, and who gets to decide that?

Let's maybe not give tax cheats any more ideas. ;)

A valid way to use charitable donations to benefit yourself is to donate assets that have increased in value. That has benefitted a lot of museums and donors.

You can also avoid capital gains taxes by donating appreciated stock. You get credit for the value at donation, potentially also lowering your tax burden.

This all makes more sense if you actually pay taxes, a burden which the GOP has long endeavored to remove from the wealthy.

@May , I can’t argue either way . I asked him about doing a Roth IRA I don’ t remember what he said . None of this is fair . My CPA just answers when I complain . Everyone pays taxes , get over it . Like Todd Snider says , these politicians promise us whiskey , then we don’t even get a beer .

I think that you better have documentation that the recipient of a "contribution" is a valid, charitable organization/recipient in the event of an IRS audit- especially sizeable ones. There are rules for charitable contributions. Small amounts don't necessarily raise any eyebrows but a $5,000.00 amount is a different story.

One of my finance instructors told us that if anybody ever "needs" a tax write-off to send him the money and he'd provide a document indicating that the contribution/investment was lost and you could write it off as a legitimate loss.

"You don't make charitable contributions to help your financial situation, you do it because you want to help the recipient of the contribution."

I think another potential situation is to attempt to classify money you'd be spending anyway as a charitable contribution to give yourself a discount.

Or better yet funnel said charitable contribution to something that ultimately benefits you, such as one that buys advertising from your company.

Right.

Assuming you are in the highest Federal tax bracket, a $5,000.00 charitable contribution to reduce your taxable income amounts to a $1,850.00 tax savings (less if you're in a lower tax bracket).

Notwithstanding state income tax (if any) your cash/bank balance is $3,1500.00 less than if you hadn't made the contribution. You don't make charitable contributions to help your financial situation, you do it because you want to help the recipient of the contribution.

I had the conversation multiple times with my dad who was told by an advisor, who charged for his services, that he should always have a home mortgage because the interest was tax deductible. This in spite of the act that he had sufficient cash to have paid off the home. Doing what the advisor told him coast him tens of thousands of dollars over the period I argued with him about.

The bank and the financial advisor made a nice income on the advice.

FunFor - "He said a way that would help me is give 5000.00 to a charity when I get there. "

Unless you file a long form (i.e. itemize), I don't see how that will help either. Either way, it's costing you thousands of dollars, but if I could, I'd much rather give it to a charity than the government.

@Maye , you are correct . I am not there yet but have talked with my financial guy . He said a way that would help me is give 5000.00 to a charity when I get there. I don’t know how that will work but I just do what he tells me.

ht tps://w ww.youtube.co m/watch?v=l0zaebtU-CA

There’s an old Sicilian proverb: “you don’t throw away your old boots until you have the new pair.”

With donald, he wants to discard what other people have accomplished without having any equivalent replacement other than a sales pitch.

Re: taxes

I think at least one area where people get really screwed is that you pay SS taxes, then you potentially pay taxes on your SS income when you retire and collect. Trump campaigned on the idea of no tax on SS income, but of course that got pulled from the big ugly bill just before it passed.

At a minimum, they should have raised the income level where you start paying taxes on SS income to be the 2025 equivalent of the $32K (joint filer) in 1983 when this tax was imposed. That would be ~$105K. This should also be adjusted for inflation rather than be a fixed amount year after year, but of course that didn't happen either.

Then, when you're 73 and have to add in RMDs, this winds up costing fixed middle-income people thousands a year in federal taxes when they're on a fixed income. Retired middle-income Americans got fucked again. Nothing new.

FWIW - This isn't a Trump thing or even a party thing as this has been this way since 1983 and every politician since has kicked this can down the road ever since.

My bad. I should have clarified that i meant POST and not thread.

"You’re in a thread started by nihilists."

I'm a nihilistic mystic... an apostolic alcoholic... a messianic manic.

(Sorry - it's from a song)

I couldn't agree more...