The contractor doesn't have to be named and associated with the permit until the billing statement is ready for issue.

If you have a $300 plumbing bill, you are another $300 in the hole.

Be clear that you are not messing around, have some wiggle room and grace, but that you have bills to pay too. 

The tax bill will be spread out because you are not collecting all the money at once.

My water usage bill is the same,  general lability coverage is the same, if and when I have to replace my water service line it will cost the same, the cost for my lawncare and snow removal costs the same, exterminating services cost the same and the list goes on.   

Progress payments, AIA billing, etc. 

With the wealth of information available on BiggerPockets and numerous other sites and books, I'm not sure where to start.

Quote from @Bill B.: If there’s nothing in the HOA about outside smoking then her telling the HOA is the same as her telling her friends.

If you're familiar with stock options, this is exactly how call options work, although they only go out a max of maybe 27 months or so.My questions are a bit numerous, but I've ordered them roughly in order of importance for me: -Is this legal?

One to hold all the security deposits and the other for collecting rent and paying your bills.