I believe Bing Maps (BingMapsTileSource) supports SSL, by the way.

Here's how you might proxy the requests for the tile images through a secure site you host.
Before you proceed in this manner, please check to see if this is a valid usage of OpenStreetMap according to their terms of use.
Also, be aware that since you are basically proxying all the OpenStreetMap image traffic for your application, that you would be increasing your site's bandwidth consumption considerably.
Also note, if this is a publically accessible site, you will want to secure access to img.aspx to prevent access to the image proxy from applications other than your own.
Unless you do this you may end up with other people chewing up your bandwidth!

The Xaml:

        <ig:XamMap Name="xamMap1" Loaded="xamMap1_Loaded" >
            <ig:XamMap.MapTileSource>
                <local:ProxiedOpenStreetMapTileSource />
            </ig:XamMap.MapTileSource>
        </ig:XamMap>

The code behind:

    public class ProxiedOpenStreetMapTileSource
        : MapTileSource
    {
        public ProxiedOpenStreetMapTileSource()
            : base(134217728, 134217728, 256, 256, 0)
        {
        }

        protected override void GetTileLayers(
            int tileLevel, 
            int tilePositionX, 
            int tilePositionY, 
            IList<object> tileImageLayerSources)
        {
            int zoom = tileLevel - 8;
            //replace this with the appropriate url for your environment.
            string secureSiteRoot = "https://localhost/SilverlightApplication62.Web/";
            if (zoom > 0)
            {
                string uri = 
                    String.Format(
                    "{0}img.aspx?Z={1}&X={2}&Y={3}",
                    secureSiteRoot,
                    zoom, tilePositionX, tilePositionY);
                tileImageLayerSources.Add(new Uri(uri, UriKind.Absolute));
            }
        }
    }

and the implementation of img.aspx.
Please note that you would probably want to add some sort of caching/security here, etc, this is just a sketch.

public partial class img : System.Web.UI.Page
    {
        protected void Page_Load(object sender, EventArgs e)
        {
            Response.ContentType = "image/png";
            Response.BufferOutput = true;
            Response.Clear();

            int z;
            int y;
            int x;
            if (int.TryParse(Request.QueryString["Z"], out z) &&
                int.TryParse(Request.QueryString["X"], out x) &&
                int.TryParse(Request.QueryString["Y"], out y))
            {
                string url = "http://tile.openstreetmap.org/{Z}/{X}/{Y}.png"
                    .Replace("{Z}", z.ToString())
                    .Replace("{X}", x.ToString())
                    .Replace("{Y}", y.ToString());

                WebRequest req = WebRequest.Create(url);
                WebResponse resp = req.GetResponse();

                resp.GetResponseStream().CopyTo(Response.OutputStream);
            }

        }
    }

Anyway hope that explains how one way you might approach consuming OpenStreetMap or other services from a secure Silverlight application.
But there are additional concerns you would have to address before using something like this in production.

-Graham

THANK YOU!

This was killing me. Thanks to the fact that the source code is available to licensed users, I was able to create the ProxiedOpenStreetMapTileSource and compile a new set of DLLs.

I used a generic handler for my proxy rather than a page, though. It works very well.

Thanks, again, Graham.

An update for anyone experiencing similar problems....

Many thanks to Graham for his help with all of his posts.

I finally resolved this today (I've learnt a lot about cross domain policies!)

I am using SL4+RIA services to have my SL app consume various web services providing sensitive data over the web. Thus my need for SSL.

To resolve everything, I switched my SL app hosting to not requiring SSL and thus viewable over http:// .   But tagged all my RIA domain service classes with

[EnableClientAccess(RequiresSecureEndpoint=true)]

This automagically tells the RIA service factory to create https:// only endpoints at runtime (the WCF services are dynamically created)

and... then as suggested by Graham, the final step for me was to then create a clientaccesspolicy.xml in my website root.

This is how mine ended up looking:

<?xml version="1.0" encoding="utf-8" ?>
<access-policy>
  <cross-domain-access>
    <policy>
      <allow-from http-request-headers="SOAPAction">
        <domain uri="http://*"/>
        <domain uri="https://*" />
      </allow-from>
      <grant-to>
        <resource include-subpaths="true" path="/"/>
      </grant-to>
    </policy>
  </cross-domain-access>
</access-policy>

This file allows you to grant access to the SL app to make calls to other domains (in my case https://mywebsite/  was being called from htpp://mywebsite/

And bingo! It all works, the service calls are secure, openstreetmaps works (and the SL app loads a little quicker - over http)

So I thought I would post my findings here in case it can be of help to anyone doing anything similar.

Thanks for the advice. I understand what needs to be done now.