ColdFusion with IIS URL Rewrite - Page never finishes loading

Question 1

Since IIS URL Rewrite's outbound rules are giving you so much trouble, here is another option. Use ColdFusion to rewrite the links in onRequestEnd. This will allow you to use physical paths in your IDE, use default documents, and still get the outbound URLs sent to the browser in the desired format. I've updated my Gist with the details.

Here is a very basic approach. Turn off the outbound rewrite rule in web.config and add something like this to your onRequestEnd function in Application.cfc. (My regex is horrible, so this reReplace() pattern only partially works the way your IIS pattern did.

<cfcomponent>

    <cffunction name="onRequestEnd">
        <!--- Get the generated output --->
        <cfset var output = getPageContext().getCFOutput().getBuffer().toString()>      

        <!--- Apply outbound link rules --->
        <cfset output = reReplace(output, '/info\.cfm\?subjectid=([^=&amp;]+)', '/info/\1', 'all')>

        <!--- Clear the previous output and send the rewritten output in its place --->
        <cfcontent reset="true">
        <cfoutput>#output#</cfoutput>

    </cffunction>

</cfcomponent>

This won't perform as well as the URL Rewrite module in IIS, but it will give you everything else you are trying to achieve (once you get your regex tuned up).

Question 2

I was able to get your outbound rules to work pretty much as is on my local dev environment (although running CF9). The only trouble was getting the outbound rules wrapped in the correct XML elements.

After that, IIS told me outbound rules could not be applied to gzipped content, so I had to add <urlCompression doStaticCompression="true" doDynamicCompression="false"/> to the configuration.

With that in place, the outbound rewrite worked perfectly. I even ran it against a page that had over 20,000 links, and it handled it fine.

Here is my <rewrite> section for web.config along with the <urlCompression> bit:

    <rewrite>
        <rules>
            <rule name="Rewrite Info" enabled="true" stopProcessing="false">
                <match url="^(.*)/info/([^/]+)/([^/]+)/?$" />
                <conditions logicalGrouping="MatchAll" trackAllCaptures="false">
                    <add input="{REQUEST_FILENAME}" matchType="IsFile" negate="true" />
                    <add input="{REQUEST_FILENAME}" matchType="IsDirectory" negate="true" />
                </conditions>
                <action type="Rewrite" url="{R:1}/info.cfm?subjectid={R:2}&amp;nameid={R:3}" appendQueryString="true" />
            </rule>
        </rules>
        <outboundRules>
            <rule name="Rewrite Info Page" preCondition="IsHTML" enabled="true" stopProcessing="false">
                <match filterByTags="A" pattern="^(.*)/info\.cfm\?subjectid=([^=&amp;]+)&amp;(?:amp;)?nameid=([^=&amp;]+)$" />
                <conditions logicalGrouping="MatchAll" trackAllCaptures="false">
                </conditions>
                <action type="Rewrite" value="{R:1}/info/{R:2}/{R:3}" />
            </rule>
            <preConditions>
                <preCondition name="IsHTML">
                    <add input="{RESPONSE_CONTENT_TYPE}" pattern="^text/html" />
                </preCondition>
            </preConditions>
        </outboundRules>
    </rewrite>
    <urlCompression doStaticCompression="true" doDynamicCompression="false"/>

I found no difference in the result when including <cfheader name="Content-Length" value="#getPageContext().getCFOutput().getBuffer().size()#" /> in onRequestEnd.

However, since you are getting the spinner and the page never seems to fully load, you might try explicitly flushing and closing the response in onRequestEnd to ensure the handoff back to IIS is complete:

<cfscript>
    var response = getPageContext().getResponse().getResponse();
    var out = response.getOutputStream();
    out.flush();
    out.close();
</cfscript>