I have a preference w/vinyl siding because of the MULTITUDES of 'looks' the industry offers. You can get shake-looking siding.
The only maintenance I know w/vinyl is you have to periodically clean it. Some need a yearly cleaning w/a power washer, others can go years (like me.) I have white vinyl siding, no trees, and low-growing vegetation. Since I get decent air flow and sunlight, I don't have the mold and mildew issues associated w/it if I didn't have my conditions. I did clean the back of the house (the North side) because it stays damp back there. There's good airflow but I do get some mold/mildew. Other than that, I don't do anything to it.
The maintenance-free aspect of vinyl allows me to spend that much more time w/my family. I do value that. I think the only problem you'll have w/your project is for EVERYONE to come up w/a common style of siding. If you stick w/a cedar-looking siding, than your problem is solved. HOWEVER, if folks like the clapboard or gingerbread look, then you're in for a fight. So, keep an open mind and think about how to handle this.