Agree it's a pain. We have all those parts but RR retirement but have rental income instead. I deal with it thru TurboTax vs. handing it all to someone to do because I want to know what's going on. Probably spend 20-30 hours on it all together.I have some complex crap going on in my taxes. Sherry has some IRA's, I have some IRA's, I have a 401-K, we have stocks, we each have accounts with Edward Jones, I get a pension and to top off the impossible things to figure out is I retired from the railroad and I get the old railroad retirement. So on the 1099 I have four parts. The top one is called the 1099 and the bottom is the RRB-1099-R. The numbers don't match up and it is a nightmare to make sense out of it.
It also makes it hard because we have to pay taxes quarterly, so the pain never goes away. It is there 4 times a year. To make it even worse we are on the hit list because we were in the Rand Paul group the IRS has declared war on. No matter what we do it will be wrong. We have been penalized one way or the other since 2010 returns because we were involved with Rand's senate run. They say I am lying but I was never dinged by the IRS until then and it has not stopped. The 2019 returns we had been forced to overpay the quarterly amounts and they agreed that they owed us over $2,000, but they have never paid us.
The IRS can be used as a weapon. Don't ever doubt that.
We don't make estimated tax payments. Never have in the 10 years we've been retired. We pay it all from our IRA withdrawals. The RMD's are larger than the tax amount so we don't have to take out more than the RMD for taxes. If you pay the taxes from the IRA, RMD or not, you can do it just once a year because the IRS considers IRA withdrawals, regardless of when or how many or how much each is, as being paid equally throughout the year. So normally pay one big lump in Nov. or Dec.