Quote Originally Posted by Suppressed Poet View Post
I sold an investment property last year. Needed cash to pay my oldest kids college tuition & expenses (just 1 more year left until they are off the payroll), home renovations, wife wanted/needed a new car, etc. Despite my every attempt to document & maximize every expense to deduct (hide) what I profited off the sale, I still had a good bit of capital gains tax owed. I’m with you on waiting until the day taxes are due before they get my money, except I kept a reserve in a MMA for this purpose.

My tax bill was less than I thought it would be, but still… Something about the painful act of writing a check to the IRS makes me want to go dump tea in the harbor. Our government legalized armed robbery back in 1913. Fuck those dickless monkeys at the IRS.
Yeah, they get you every way they can. We paid taxes when we earned the money that we invested, we pay taxes (more) if we make money on the investment and it's short term, still pay taxes if it's long term. Nevermind city, state and local tax.

I know, go IRA. My company didn't offer an 401k Roth until about 6 years ago, since then I have, and I'm old enough I'm in "catch up" years so I can put more than 23.5k (I can do 31k this year). Regarding a straight IRA I'm old enough I can do 8k there and my MAGI is enough I can do even more than that. I was dumb when I was younger and had a straight pre-tax investment account. Now I'm maybe 70% 401k, 25% 401k Roth, 5% IRA.

I need to talk to a retirement expert though, we've decided my wife is retiring in 3 years, I WFH so I'll milk this job until I'm tired of it, then retire. We owe nothing anymore, so it's really a lifestyle choice at this point what we do next. I like my job and the income that comes with it, so I'm lucky there.