We know the march toward subscription-based software is inevitable. But, I'm trying to hang on for at least a few more years.
* Adobe Acrobat
I still have a licensed version of Acrobat Pro XI. Trying to install it on my new machine was a real pain and time-waster, ever after I de-activated my license on the old machine. My Adobe account showed I was fully licensed for this version, yet the license key would not work. Turns out I had to go back and re-install Adobe ver. 9 first with that license, then I was able to apply the newer license with the new software. In the meantime, in desperation I decided to try the cloud-based subscription. They want $15/month, with no discount for paying a year in advance, so I paid for one month. Then, once I finally got the desktop version working, I went to cancel -- first thing the Adobe web site offered me to get me to change my mind was two months for free ($30 discount!!). Amazing. But, I still canceled, and allegedly I will get a refund of the $15 (I never used the software).
* Microsoft Office Home & Business (the version which includes Outlook, which I use for calendaring)
The last-ever version for desktop is 2019, for which support ends in about six years, I think. I currently have Office 2010, which reaches end of support in 2020. My 2010 license for a incremental fee allowed for use on two machines, but now MS no longer offers that, so I would have to buy two licenses at full price ($200-249 each, depending on where bought). That really sucks, but I might do it just to get that extra six or so years of support (security patches), by which time I probably won't be doing much professional tax prep if any.
Quickbooks
Shamefully, the still haven't fixed the simple "output to PDF" function even after more than seven years. Here's what QB expert Charlie Russell wrote seven years ago, and it's still true now:
"I’m not sure why Intuit has had so many problems with “PDF Drivers” over the years, but this has been one of the constant thorns in our side, as users and advisors. Can’t they just fix this in a simple way? We just want to send forms and reports to a PDF file. I have to tell you, with my own software, I have a simple PDF driver and I never have any trouble like what we’ve seen in QuickBooks!"
I spent over an hour on the phone with Diamond level support (I'm a ProAdvisor), and tried every one of the dozen or so things they suggest for fixing this (after discovering that the only way I could even view the web page with support links was using MS Edge browser, as both Firefox and IE could not display Intuit's poorly configured web page).
This prevents me from generating invoices in my QB 2019 software with a payment link for QB Payments. I still have two older computers where it works (although those were upgraded to Win 10, unlike my new machine). I will probably have to use QBO solely for the purpose of sending online invoices -- I guess I can just upload my client list in order to create the simplest possible online invoice, and still send the "real" invoice from my desktop software as an attachment.
Tax software
I paid for ProSeries through TY2014, but I'm not going to try loading it on my new machine. But even if I did, could I still open tax returns that I paid for (PPR)?
What about UltraTax? Now that we have to log in to use it every time, what happens if I stop buying the software in future years, can I still open my older return files? I could not even install the software without an internet connection, even thought I had a full offline install copy and license file.