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We have listed several types of upgrades that are available and have included the reasoning behind each upgrade.

Community 1.XA to Community 1.XB In this upgrade path the reason may be to keep the current 1.X theme and extensions in place while upgrading the backend code to a newer version of Community 1.X. This tends to be the lowest cost with the fastest schedule. This upgrade can sometimes takes advantage of newer versions of code, fixed bugs, memory utilization improvements and security upgrades.

Community 1.X to Community 2.X In this upgrade path the reason may be to get on the latest version of Magento Community and take advantage of the newer technology. The cost tends to be equivilent to building a new Magento site. The reason for this is that the 1.X theme, extensions and customizations cannot be just "migrated" over to 2.X. It's technically a new build which includes a new 2.X Magento theme. The cost savings over building a new site is that the database can be migrated over with Magento's migration tool to 2.X and, if the requirements all remain the same, saving time without having to do another deep discovery of requirements. At this stage of an upgrade it's worth considering what extensions you really need to move to 2.X. Doing a refresh on the frontend store design including adding responsive design if it was not on the 1.X site.

Community 1.X to Enterprise 2.X In this upgrade path the reason may be that your Community 1.X site is maxed out with some capabilities. By upgrading to Enterprise 2.X, you take advantage of not only the new 2.X platform but also the benefits of Enterprise. This cost tends to be almost equivilent or slightly higher as building a new Magento site. The reason for this is that the 1.X theme, extensions and customizations cannot be just "migrated" over to 2.X. It's technically a new build which includes a new 2.X Magento theme. The cost savings over building a new site is that the database can be migrated over with Magento's migration tool to 2.X and, if the requirements all remain the same, saving time without having to do another deep discovery of requirements. At this stage of an upgrade it's worth considering what extensions you really need to move to 2.X. Doing a refresh on the frontend store design including adding responsive design if it was not on the 1.X site.

Enterprise 1.X to Enterprise 2.X. In this upgrade path the reason may be that your store is ready for a major improvement or you simply want to take advantate of the new Magento 2.X platform. By upgrading to Enterprise 2.X you take advantage of the new 2.X platform. The cost tends to be equivilent to building a new Magento site. The reason for this is that the 1.X theme, extensions and customizations cannot be just "migrated" over to 2.X. It's technically a new build including a new 2.X Magento theme. The cost savings over building a new site is that the database can be migrated over with Magento's migration tool to 2.X and, if the requirements all remain the same, saving time without having to do another deep discovery of requirements. At this stage of an upgrade it's worth considering what extensions you really need to move to 2.X. Doing a refresh on the frontend store design including adding responsive design if it was not on the 1.X site.

This is a tough question to answer without having any details. Every Magento Community site is different so here are a few things to think about when asking this question.

  1. Most stores that may do 1-100 orders per week are fine with Community, but in some cases stores doing this quantity could benefit from Enterprise.
  2. Most stores that do an online annual revenue of less then $2M are fine with Community, but in some cases stores doing this revenue could benefit from Enterprise.
  3. Enterprise should be considered when a good percentage of the Enterprise Only features will be utitlized.
  4. Enterprise should be considered when there are sites that process dozens of orders in a duration of only a few minutes. This could be due to a big sale or promo that is pushed to the public.
  5. Enterprise should be considered if another technology is required that only integrates with Enterprise.
  6. Enterprise should be considered if growth or expectations around a new site deem starting with Enterprise necessary. There will be double cost and schedule impacts to your business if you start on Community and then require Enterprise for any reason within just a few months.

There a many reasons to upgrade to Magento 2.X. The first is that new platform is a redesign of the platform focused on the future. Benefits can be found here https://magento.com/products/enterprise-edition. Whether going from CE 1.X to CE 2.X or EE 1.X to CE 2.X getting on the next platform version positions your business for the future and benefits of Magento 2.0.