.#1, 2 and 3 all have first class stamps and are hand-addressed.4.

If you like the look of pavers, why not do stamped concrete as it can give you a similar pattern?

You can't triple stamp a double stamp.With the right collateral and debt/income levels to satisfy a lender, sure, you could do that.

I'm thinking of replacing the bricks with a stamp concrete design or perhaps restrain the existing brick.  

This can be very useful in states that charge taxes / stamps / fees for recording mortgages / deeds.

You just have to make sure your plans are right, you have the right stamps, and the people you are working with know what they are doing.

After I got home I see my Tenant left a letter (presumably with the motion for more time) with no stamp at the main door to my apartment building (12 Units).

Everything is hand addressed and hand stamped and written in blue ink.

I sent out a similar number of mailers and was able to write a somewhat personal sounding letter, return address it with a local address, use stamps I stuck on myself, and make it look the opposite of a direct mailer.

@Schelley Stamps What do you want your software to do?