I would create a site for home building, include your garage building and remodeling services here, a separate site for roofing and include your exterior services here, gutters, siding, soffits, etc... That is easily two 50 page sites (including blog posts) if you wanted them to be.
As for the Places Listings. You could create separate +pages for each business.
Fowler Custom Homes and Remodeling
Fowler Roofing and Siding
If your businesses share an address then you need to send very strong signals to Google that they are indeed separate businesses.
- Each business has a different name.
- Each business has it's own phone number.
- Each business will be in it's own categories (home builder/roofing)
- Each business will have it's own domain and website.
That sends a pretty strong message that the businesses are in fact different, even though they share a physical address. That's one way you could do it. Silo sites etc... I wouldn't even worry about the concept it's so pumped up right now by SEO gurus and information sellers that I imagine the next update or two will wipe it all out lol.
Any suggestions on what to do would be greatly appreciated. Thanks in advance guys.