Yeah, as
@Westernhawk stated, Trump has been proven over and over to be a serial liar, so what he says carries very little weight. For example, he has said no cuts to Medicaid, but he supports a House Bill that includes 100's of billions of $s worth of Medicaid cuts.
The no tax on tips thing is worth discussion, but it is probably a bad idea, and the situation (gratuity-based workers barely scraping by) would almost certainly be better addressed by eliminating the "tipped minimum wage." Numerous economists have made convincing arguments, and several natural experiments (several states have eliminated the tipped minimum wage) support these arguments. Also, eliminating income tax on tips would open doors for more tax evasion, as many in the service industry would change fee-based services to tip-based services to avoid taxation.
I don't know much about the notion of eliminating tax on overtime, other than it sounds like an enormous oversight burden. Beyond that, his prior statements do not lead one to believe that he actually has much concern for laborers working overtime:
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I also do not know much about eliminating taxes on social security. It seems kind of messed up that those are taxed at all, but I would guess most social security recipients pay little to no taxes unless they are also working or on the high-end of recipients, in which case perhaps it makes sense.
But regarding the effects of his tax policy proposal on the various income divisions, listen to the economist's take on tariffs I posted yesterday. Analysis of his proposed tariff plan (he is constantly revising it, so hard to pin anything down) suggests that most Americans will experience between a $1,200 - $2,000 per year cost of living due to the tariffs. His proposed tax plan would save $1,000 per year for the median household income. Thus, the median household and below lose out with his proposals.
The further you go down the income distribution ladder, the worse things get. Their savings will be even smaller because they already pay little to no tax, but the cost-of-living increases will persist. They will also be more greatly impacted by the degradation of services that are the natural result of the massive cuts to the federal workforce and entitlements, as they were often the recipients of these services. This will have a massive impact on poor children, in particular, who will have less access to healthcare and early educational enrichment, further entrenching them within their class and stifling the upward mobility that we think of as a hallmark of Americanism (that Horatio Alger story has always been harder than we pretend it to be, but these changes will make it significantly more difficult).
In contrast, the top1% of the income distribution stands to save about $70,000 per year with Trump's proposed tax plan, and their cost of living increase will be roughly the same as the median household. With tariff's being largely a consumption tax, those higher in the income brackets can avoid it by simply spending less and saving more. Those at the low end of the income brackets CANNOT do this because their income goes almost 100% to cost-of-living; that is, they spend only because they have to, and they do not have the option of simply spending less and saving more.
Hopefully that helps to explain why Trump's tariff/tax plans are considered regressive (have a bigger burden on the lower income brackets) by every single objective analysis.