Hosting Options
Editions & Hosting
There are different editions you can make use of, Odoo Community and Odoo Enterprise
Odoo Community
Selfhosted
Docker
No
On Premise - You install it on a server you own or rent
Odoo Community
Odoo hosting platform
Odoo.sh
No
it's a SaaS on Odoo's servers
Odoo Enterprise
Odoo hosting platform
Odoo Online
Yes
It's a PaaS on Odoo's servers
Modules / Apps
These are the different module options:
Official
aka Standard
All standard modules are covered for maintenance and upgrades by the Odoo Enterprise agreement. Some of them are available in Odoo Community edition; all of them are available in Odoo Enterprise edition
Mostly
Community
aka Third Party
Are available via the Odoo Apps Store and not covered by the Odoo Enterprise agreement
Sometimes
Plans
Free plan
aka. freemium
Available only on Odoo Online hosting if you use 1 app only
Conditions apply
Standard plan
available only on Odoo Online hosting
Custom
available on all 3 hosting options
Now that we have established this terminology, let's address your questions:
Questions
Question:
I would like to know if I should pay per user via the official Odoo site or setup my own install on a hosted server.
Answer:
The moment you will pay for Odoo Enterprise, you will necessary pay per user, so there's not really an alternative to pay based on a different metric than users. Hosting on your server (ie. On Premise hosting) doesn't dictate if you pay or not. The edition you use dictates if you pay or not. You can use Odoo Community or Odoo Enterprise on Premise.
Question:
Do I get access to all the apps seen in the paid version on the self-hosted install
Answer:
Yes, all the standard apps. Not the third-party apps.
Question:
If so does this include the additional plugin apps?
Answer:
If what you mean by "additional plugin apps" is third-party modules, then the answer is no. There are 40,000+ third party apps on the Odoo Apps Store. Some are free and some are paid.
Question:
What are the pros to paying per user, seems like this will get wildly expensive once the business grows so starting with it being free just makes sense, no?
Answer:
Either you use Odoo Community for free, or you use Odoo Enterprise with the Free plan for free, or you use Odoo Enterprise and you pay for it per user. The pro of paying for Odoo Enterprise instead of keeping your Free plan is that the Free plan is limited to 1 app only. So, you can use your 1 app free plan with Odoo CRM with as many users for as long as you want for free, but the moment you will install a second app you will have to pay Odoo Enterprise for all your users.
Another pro of paying for Odoo Enterprise is the ability to use it On Premise, which seems to be what you want. The Free plan is only available on Odoo Online hosting.
Question:
Can you migrate data from the paid to a self hosted setup down the road?
Answer:
Odoo Community is the same product no matter where you host it, and Odoo Enterprise is the same product no matter where you host it. So if you are using Odoo Enterprise on a certain hosting type, you can back it up and restore it on any other hosting type. Keep in mind that it's easier to go from Odoo Online to SH or On premise than the other way around because there are more constraints on Online than on SH and On Premise. To answer strictly to your question: yes you can go from Online hosting to On Premise hosting easily down the road.
Extra info:
Hosting
https://www.odoo.com/page/hosting-types , https://www.odoo.com/blog/business-hacks-1/how-to-choose-your-hosting-type-560
Transfer hosting
https://www.odoo.com/documentation/latest/administration/maintain/hosting_changes.html
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