You haven't indicated any properties of the clayey till - i.e., liquid limit and plasticity index - typical Ontario silty clay to clayey silt tills are usually in the 10 to 15 range. Obviously you must have some lab data if you know the existing materials are significantly above optimum moisture content. You have not mentioned either how thick the fill will be. Based on your post, the underlying materials would be, for all intents and purposes, incompressible (I would assume that the N value of the natural till is greater than 15 to 20) so I am wondering why the residential housing is on piles. Is this for high rise apartment buildings or single/double storey residential housing? Are the piles to be installed "deep" into the underlying till/mudstone? What type of piles - driven or bored? I wouldn't mind seeing some of these details.
So the real question may just be the compressibility of the fill - under the roads if compacted to 95% standard Proctor within a couple of percent of optimum, I wouldn't see 5 m of fill causing any problems with settlement over the long term within the fill itself - so the roads, kerbs, etc should be okay. If the soil is wetter than that, you should give consideration of aerating it to reduce the moisture content. There are other toys that could be used. Make sure you put in joints at 2 to 3 m for the kerbs if done by slipform kerbing machine. As for downdrag on the piles, I would think that the fill wouldn't settle sufficient for any major downdrag forces - and if the pile tip can "give" a bit, it would be less. You can look up Fellinius to see what downdrag might have/occur.
Just some thoughts - provide some details as noted in the first paragraph and you might get some better response.