These are my suggestions:
1) Sizing for the VM - I would first direct you to the release notes for your version of the PI Server (a.k.a. PI Data Archive) and this "Hardware and PI System Sizing Recommendations Spreadsheet" published by OSIsoft. Each version of the PI Server has specific RAM, and hardware requirements. Next, I assume you mean the size of the virtual hard drive or available storage for storing your pi archives. There are some guidelines that can help. Determining the size will have a lot to do with how quickly you can fill a 256 MB pi archive of process data. If you fill it in an hour you need bigger archives. If it takes you weeks or months to fill it you can stick with that generally suggested starter size. Next, how much history do you want stored directly on your PI Server? So for example you want at least 5 years of data and it takes you one month to fill 256 MB. So 256 MB x 60 months = 15,360 MB (15.4 GB). Unless you are leasing the VM from a provider who charges by the GB why not set it up for 50 GB so you have lots of room to play.
2) Writing PI Data to an Oracle DB and a Web Server - There are lots of ways to export PI Data for sending to other tools and applications. The myriad of options include PI OLEDB, PI JDBC, PI Web API, etc. You can find out more about these PI Developer Technologies at https://techsupport.osisoft.com/Downloads/All-Downloads/Developer-Technologies/All-Products. With a little bit of research and effort you can use SQL query language to 'SELECT' PI data and 'INSERT' it into an Oracle Database, or export it to a web server in your choice of formats. You can also consider building a basic application utilizing the PI AF SDK to export, manipulate, and send data. There are a lot of options here.
The deployment I am currently preparing to deploy will be in a test enviorment and in the future will cut over into production.
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Welcome to PI Square and to the PI Community!
I would recommend that you have a look at the following article:
Also, make sure to read the PI Server Installation Guide and AF Installation Guide before proceding.
Most of our documentation can be found in the LiveLibrary.
Also you can search on PI Square and the Technical Support Web Site to find the information you are looking for.
If you have questions, the Technical Support is there to help. Make sure you prepare well and I would encourage you to call the support the explain your strategy before you proceed, that may help you and answer many questions.