Nice writeup and plenty of good points made. However, the author left out one huge item in terms of why On-Premise is challenging: ongoing support and maintenan

Nice writeup and plenty of good points made. However, the author left out one huge item in terms of why On-Premise is challenging: ongoing support and maintenance. I was an engineer on a product that had an On-Premise (OP) offering. Some of our biggest moneymaker accounts were On-Premise and liked the product. The downside was that we had to have a dedicated team just for On-Prem stuff. I was one of the engineers on that team. We had to develop custom management interfaces for the software that were only deployed in an On-Premise environment. It wasn't crazy hard or anything but it was time and effort. Upgrades and installation were also a big track of work unto themselves. When you deploy into an On-Premise environment you are completely at the mercy of the clients infrastructure. One support call I did was clocked at 14 hours - there are so many things that can come up. Plus there's the whole hassle of actually getting the calls scheduled and making sure clients aren't too many versions behind. Sometimes we had to spend a lot of time waiting on support calls because the customer didn't have their stuff together. Like sitting and waiting for a network team to open up the firewall so that bits could be downloaded from our distribution server. And of course the firewall had to be closed up right afterwards, so this was a common thing. Another time we spent weeks troubleshooting a client installation. In the end it turned out that the client had our software talking to two different internal NTP servers which were slightly out of sync, which caused our SSO/SAML integration to break. Database migrations were also challenging - in a cloud environment you often have flexibility to migrate things live while the system is running. But often with the on-premise upgrades, you had to take the whole system down while the migration was running (back to the 14 hour support call). This could mean scheduling the support calls at really weird hours. On-premise also has challenges if you start selling to the US government, especially defense. There are super strict requirements that support personnel must be US citizens on US soil - so hopefully you have more than one person on the team meeting this requirement! All in all, I am not a detractor of offering an On-Prem solution. It can be a real differentiator and it will open a lot of doors. There are some companies that simply won't buy SaaS, either due to internal or regulatory reasons. Once you land these clients it can be very lucrative and long-term. But, it almost always requires dedicated staff to support and manage.