What service/professional do you use for tax preparation?

[FIRE Realtor]

In past years I had a very straightforward situation and did taxes myself with Turbo Tax, thought it worked out fine. 

In 2019 I got divorced, am self employed (low income ~ 12K /year), bought a new house with my fiancee, and am renting out my previous house which I am sole owner.  (Rental income is separate from my other income, which is from doing child care). 

My fiancee is partner at his law firm (~200K / year), had someone prepare his taxes for a few years but didn't like him, thought he was disorganized.  He's ended up paying in tens of thousands at the end of the year and would like someone who knows best what to do when dealing with lots of extra income. 

We are planning to get married in 2020 and want someone who can advise us on how to best set up our financial lives in terms of taxes. 

Any recommendations for certain software, professionals to consult, or just resources for us to educate ourselves?

[MustacheAndaHalf]

The most complicated thing you mentioned is rental income.

"H&R Block Deluxe" handles rental income.
On Amazon, TurboTax support said "Please consider 2019 TurboTax Premier to report on your rental property."

In general I expect tax software to make fewer mistakes than a tax preparer.  But I don't care about being aggressive or not - I prefer to be very conservative with the IRS.  Even with complicated situations, I prefer to stick with tax software.

If you think it's appropriate for both you and your fiance to know each other's finances, you could go through some of the tax stuff together with tax software.  It's probably not an ideal fiance activity, but it's important to know about each other before tying the knot.  And you might be able to make it a little less frustrating, by helping each other (or helping each other blow off steam).

[habanero]

I find the tax preparation discussions deeply fascinating....

We have a fairly standard personal economy - we have a jobs paying income, we own a house, we have kids, we have a mortgage, we own a car, we own index funds, I have some single-name stocks, we have bank accounts, carry some balance on credit cards at year-end most likely, my SO still have some student debt left, I might or might not have bought and/or sold some single-name equities during the year, I get some dividends, we pay some for social security, we pay taxes via our work, my country has wealth tax, unions payments are tax deductable, so are interest payments on debt, we pay some property tax etcetc, there are some extra deducatbles for kids and some extra government payouts you get for kids etcetc - basically all the usual stuff from living a fairly normal adult life in a family.

Come tax time and it's time to file. I have to do abseloutly nothing. As in nothing at all. Everything comes pre-entered from the tax office - I check the numbers but every single one of them has been 100% correct for the last 10 years. I think I have to actually file which means logging onto a web page and click a button (not sure, think maybe if you don't do anything you are assumed to agree), but you can correct stuff if you have to. The whole process takes a few minutes if everything is fine and a few more minutes if you have to correct something. The entire idea of needing special software or even hire someone to do taxes for you is utterly bizarre to me

[reeshau]

The entire idea of needing special software or even hire someone to do taxes for you is utterly bizarre to me

As would, likely, the concept of doing so to turn a 22% total income tax rate to as low as 0%...

I find the same situation in Ireland.  Amazingly, there are tax deductions here you can take for medical expenses and charitable giving.  But most people are entirely unaware of them.  Taxes are high, and simple.  That is the accepted truth.

Also true:  the only thing worse than a tax man are two tax men.  I live at the intersection of the Irish and US systems, and hope to almost be through my 2018 return process.

[MustacheAndaHalf]

The simplest tax system sometimes appears in jokes about the IRS:
"How much did you make last year?  Send it in."

The IRS could actually calculate people's taxes.  But money has corrupted politics, and so the companies that sell tax software also give money to the US Congress to prevent taxes being simplified, and prevent the IRS from doing the calculations.

[LightStache]

He's ended up paying in tens of thousands at the end of the year and would like someone who knows best what to do when dealing with lots of extra income.

How much you can do really depends on you fiance's desire and ability to optimize the partnership's financials. If he has no say in corporate financial management/compensation structure, there's not a lot to do, otherwise the sky's the limit. So my primary recommendation would be to have his firm hire a tax strategist that also advises the individual partners as a perk (this is common).

If that's not possible, then you could shop around for a personal tax adviser, but if you're not tax-savvy it will be challenging to know if you have a good one.

Regardless of the above two options, the best thing is for you to get smart on tax! If your childcare business is part-time, you could probably get spun up to do remote tax prep as well. That would bring in extra income and set YOU up to be the family's tax adviser.

Before you get married, make sure you have an asset protection strategy in place related to both your rental and child-care businesses. You don't want your combined future earnings at risk because you have two high-litigation-risk businesses.

[Lucky13]

My fiancee is partner at his law firm (~200K / year), had someone prepare his taxes for a few years but didn't like him, thought he was disorganized.  He's ended up paying in tens of thousands at the end of the year and would like someone who knows best what to do when dealing with lots of extra income. 

A few years ago I had a bad experience with a tax preparer and got mad and decided to do it myself. :D  I do have a CPA review my return, after I complete it, so I'm only paying for 1 hour of their time instead of doing the entire thing, so that's something to consider too. I use Turbo Tax (which is what the pros use anyway).