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This is very important, since an estimate is just that. Many contractors will submit a "paper estimate", meaning they've written the estimate down on paper. The bill is the true amount owed and will almost always say "Invoice" or "Bill" at the top of the page. The bill should also list the date it was issued, the due date of payment, and a list of services rendered.
Many jobs in Florida will require municipal permits in order to be approved by the town's inspector. It's always good to ask who will be responsible for pulling those permits, and if you'll be expected to do it. You'll almost never be told to pull your own, but knowing that Naples Windows permits are required makes you appear to be a well informed customer.
Some companies may require a 10% deposit, some may not require any. For larger projects, you'll almost always need to give a deposit, and it's good to ask how much the deposit will be before going forward with a project. The Naples contractor will know how much they need for a deposit when they've given you the estimate, so ask early.
This really only matters if you have a preference, but it is good to ask. If you have a strong ideological belief about unions or nonunions, it's perfectly acceptable to make a decision based on the preference.