How to distribute an installer which contains a bootstrapper
Due to severe limitations of the Microsoft Windows Installer (MSI) system it is required to create a bootstrapper in order to install multiple MSI files (due to pre/post-requisites). However, this introduces an distribution problem because you now have multiple files that need to be included with the distribution. There are of course multiple ways to distribute this as a single file.
1: An archive
You can put all the files into a single archive that users download. The obvious choice for MS Windows is of course a PK-ZIP archive. But this is not very user friendly. Users will first have to extract the archive, and then run the bootstrapper (which would be called setup.exe).
2: A SFX archive
Instead of distributing an plain archive file you could wrap it into a self extracting archive. Executing this SFX archive would prompt the user to extract and/or run the contents. But this adds yet another prompt to the whole installation process (#1: SFX prompt, #2: bootstrapper prompt, #3: main installer prompt). This is also not very user friendly, as it increase annoyance due to multiple prompts.
3: Single file bootstrapper
Of course there is the option to embed all the extract files into the bootstrapper. This is probably the most user friendly for a normal end-user. However, this is less friendly for system administrators, because usually bootstrappers are less manageable than the MSI files. An admin would rig the system so that all requisites are also installed when the main MSI is installed, thus the bootstrapper would not be needed.
An other unlisted method?
So what do you think is the best way to distribute a installer for MS Windows software that requires a bootstrapper?
We provide a single file bootstrapper for retail distribution and all single-user installations.
Volume licensing customers (e.g. 10+ seats) receive one (or more) MSI files along with instructions and a list of prerequsites that must be installed before our application will run (which slightly differ between XP, Vista and Win2k). The EXE blocks installation if the prerequisites are not installed, the MSI will permit installation under the assumption that the sysadmin knows what they're doing and might be installing the prereq's at the same time, before the next reboot.
Basically the single bootstrapper is for non-sysadmins, people who want a single click solution. System administrators and corporate IT support who prefer more fine grained control over their installation are happy for multiple files, even if it means more work for them. The single EXE file is available publicly, the instructions + multiple files are only available by contacting our sales team.
This method gives us the best of both worlds, as well as the ability to provide different default configurations for home and corporate customers - hints, tips, splash screens, auto-updates and welcome dialogs are all disabled by default for corporate installations but enabled for "single" users.
We use Wix to create MSI files which is hugely flexible and can easily be automated with build scripts.
To chain multiple MSI/EXE files together for distribution via single bootstrapper I would highly recommend DotNetInstaller. I'm in no way connected or affiliated with this product, but it has been a lifesaver on projects for generating highly configurable bootstrappers in unmanaged code.
I wrote up my recent experiences in developing a multi-language MSI and bootstrapper using these technologies here. This talks through the process from start to finish. Using DotNetInstaller you can download and install dependencies from a URL on demand, or embed them directly within the bootstrapper with ease. I did also consider WIX's own SETUPBLD bootstrapper generator and the GenerateBootStrapper MSBuild task but they are pretty basic. That said WIX 3.5 Burn utility is currently in the pipeline and could be a pretty decent alternative once it's released.
Regarding: 1: An archive: 2: A SFX archive
You could use a self-extracting .ZIP that automatically launches a Setup.exe. WinZip offers this support inexpensively. That way, it would be more customer-friendly. It can be configured to launch the bootstrapper without a prompt.
Regarding: 3: Single file bootstrapper
At the risk of sounding like an InstallShield salesman, InstallShield 2009 will take care of everything you're asking about -- it smooths over the MSI shortcoming of needing a bootstrapper. You could use the Release Wizard to create a single-.EXE all-in-one bootstrapper. Or you could create a web-deploy setup that is very small and then downloads the payload from a web site. Or you could put different features in separate .CAB files, and the user only needs to deploy those CAB files corresponding to the features he wants to install. InstallShield comes bundled with dozens of prerequisites ready to add to your Setup.
Depending on your siutation, MSI v4.5 and 5.0 might help you -- they have native support for multi-package transaction chaining. Of course, depending on what OSes you support, you may still need a bootstrapper to make sure the right level of MSI support is present.
I had a similar problem where I needed to distribute some optional support software, MSI installer, and another file just incase the MSI file needed it. I basically created a native application to handle the whole process. I wrote a blog about it here (http://blog.foldertrack.com/?p=45)