Making the Drop (without any altercations or arrests)

So, Someone I know has a sister who is currently incarcerated in a work center for non-violent felons.
Each weekday, they all put on their state issued, horizontally green striped, pants, and walk out of the gates and into the small community to work, a mutually beneficial relationship to all.
Every Saturday, approved visitors may visit from noon to 3:30, UNLESS there are 5 Saturdays in a month, in which case they just don't get a visit that weekend.
Letters may be exchanged via the USPS, but they may only receive 2 packages a month, one for PERSONALS, and one for CRAFTS.
A routine was developed in order to facilitate the delivery of extra needed supplies and/or correspondence without having to learn how much postage stamps cost and without struggling to coordinate with the "official" monthly package, a chore that seems more suited to the personal assistant of a CEO of a large organization.
The routine seemed simple enough.   Place package in empty, white plastic planter near the back door.  Then, nest the matching planter inside, effectively shielding the package from Saturday afternoon until the inmate's return to work Monday morning.
Due in small part to an irrational, yet intense, fear of being wrongfully convicted, I arranged to be 90 miles away, with many eyewitnesses to support my alibi, during the initial "drop," all the while assuring the "droppers" that the whole thing is perfectly legal, but they might want to bring bail money, referred to as "cash for shopping, justincase!", because there are many, many bargains to be found, if you look carefully, but, under NO CIRCUMSTANCES are you to slow down, crack open a window, look directly at anyone, and DO NOT GET OUT OF YOUR CAR no matter what, while passing through the World's Smallest Ghetto.  No problems or complications were reported to me, so I assumed it was an easy process.
Helpful hint to anyone planning anything more complicated than a Taco Bell run: Arrange to have a getaway driver!  They get bad publicity, but they are infinitely more helpful during day to day operations than any heist you'll ever need to pull.
So, after weeks of carefully planning my own drop, Saturday morning found me feverishly scurrying around gathering some items (clothing, a book, a nice pants SUIT, in a separate garment bag, for goodness sakes!), packed tightly into a clear zippered bag (like the ones I save whenever I buy bed-in-a-bag sets).
Remember now that I have never seen the LARGE WHITE PLANTERS that I've been instructed to use.  The planters outside at my former home were big and heavy, like with palm trees in them, definitely not anything that could blow away.  These are similar to what I expected to find.
There were several pairs of JEANS in my bag.
The first thing I noticed when I cased the joint by driving slowly by were a few overturned, beigey looking, smallish plastic flower pots out back, by some weeds and other assorted junk.
The second thing I noticed was a ludicrous amount of police cars, scattered about randomly, as if you were about to play with all your Hot Wheels cars and dumped them on the floor, but then you got distracted because somebody else pulled out a humongous box of dress-up clothes, including tiaras and heels!
I parked behind a nearby building to get my nerves under control and to re-route my M.O.  I considered preparing a plausible explanation for my actions for my eventual arrest, but I was blanking on that.
By that point, I believed everything except the building I was trying to near-filtrate was booby trapped, alarmed, and patrolled by armed, vicious K-9s.   And possibly their officers.
In order to transfer some legally obtained, OTC meds to the drop bag, I had to pull out my giant bag of OTC and prescription meds and pour pills into different bottles, because an innate should only have pills in properly labeled bottles, right?  Of course, I'm right. 
However, not having planned for this, my OTC bottles were full and I couldn't spare all that Tylenol.  So, I opened up all my empty and partially filled pill bottles and filled them to capacity with Tylenol, all the while suspecting I was being monitored closely by cameras, dogs, and cops.
I have decided completely against leaving the nice suit.  It's started sprinkling already, and the "drop bag" will be outside for 2 nights.
I have also decided that I don't wanna join my sister in prison, even if it is the work release kind, so I drive away in what I hope is a casual, nonchalant manner, even though there's an abrupt dead end and I have to turn around because apparently they don't want you driving past their cops. Or their buildings.
I watch ALL my mirrors carefully to see if I'm being followed yet, and it doesn't look like it.  I drive on and see a THRIFT STORE!  Yay!
Perhaps I can purchase a non-clear, less permeable bag, whilst I wait out the cops.  Surely, they already ran my plates and have decided I'm not a threat to a city/federal building.
I hide out a while at the thrift store.  In fact, I stay until I hear the cashier turning customers away, saying they're closed now.
I pay for my things and transfer the clear bag into the giant, black, martial arts (cause I'm part Ninja, y'all!  What part?  The BEST PART!) nylon bag and return to the scene of my non-crime.
So I park my big blue mini van on the street, in plain sight next to what I can only describe as some kind of broken-off alley junk pile hole where the homeless might seek shelter if there weren't so many cops and questionable characters like me wandering about.
Needless to say, the flower pots were filthy, they wouldn't "nest" properly, and I hurriedly (nonchalantly, of course) re-arranged the contents of the alley, including moving their water hose caddy. 
It's one of the ugliest alley holes I've visited and I may bring paint and a graffiti artist with me the next time to spruce it up. And maybe build a small shed. I don't think you can get arrested for community beautification projects.
I swear!  ADHD and an irrational fear of wrongful arrest and imprisonment makes simple tasks so much more complicated than necessary.