Bob Fairbairn


I live and work in the USA and Tax day for me is the day I do both my business taxes and my personal taxes. I usually have to wait till about March 1st to get all the data in. This is risky with all the scammers out there,… My son just got a 1099 this week that should have been here in January!.. We have gotten three different proof of insurance forms from BCBS IL for my wife. I think they got it right the third time.

So as a macOS and iOS guy tax day for the business means I have to have a PC around because all the tax software for Buisness appears to be only on PCs. Now I have a very simple business so it is not hard. I have been using HRBlock software for a couple of years and up till this year it is just OK. This year has been terrible. I have found it impossible to move the data from one PC to a new one so that I can not be bogged down with the two year old Core i7 machine (that is a joke folks). I should have just re-entered the data instead of trying to import from last year. The program is spitting out forms that have no data on them with things like #VALUE where there should be nothing. The UI is terrible and is about 10 years old Windows style. The documentation and messaging is cryptic. But It is done. So the e-file of federal is done, with the round trip to the printer/scanner to “sign” the special form that lets you e-file. The drive to the post office is done to mail the state taxes that the software will not allow you to e-file.

—- Phase one done —-

Then I tried to use the personal software to do my personal taxes. It kept trying to update itself over and over again. It did import finally and I tried to get started. Boy was that a mistake! I do not know how may times I got the (Not Responding) messaging and could not enter data. They say that there is an update schedule for March 28th so do I have to wait to file>?? WTF??

So I abandoned ship and got the Mac version of TurboTax. And it just worked. Yes there are some cryptic questions, but hey this is the US Tax system built by folks that want to try to obfuscate things because “they can”???

Tax software is a lot like accounting software, it never works like “real people” want it to. And lets not forget payroll, what a MESS.

Now all the data is in for the home taxes and I am “cooling off” to review with my wife later.

I can dream that all of this should just go away for something simple and automated. Really folks this should not be that hard.