Satirical Vintage Comedy & Realism Artwork

Three pieces of Artwork for a shirt to project a mixture of satiricaly humorous vintage comedy & Realism if possible. 1st piece for sweatshirt back (main piece) 2nd piece is a "crest" for front of shirt top left 3rd piece for shirt front top right is artwork to look like a traditionaly embroidered name tag. The idea for the main shirtback art is a slightly higher emphasis on the man 'Pegleg' There are three components to the main piece, Land. Sky. Water. I envision the Land&Sky components taking 90% or so of the total space. The main points I can think of:). 1) Some experience in shirt art so as to advise me. The shirt colors I would prefer to ultimately wear the shirt art on are; Slate, Army green, ? Orange, Yellow, Black and White. Will it matter on the 3 or 4 colors used in the art? 2) I've researched enough to know I'm not sure what the format should be to get the finished product in? It seems like 'vector adobe' is frequently mentioned?? 3) 14" to 16" for main shirtback design. 6" or so for the front crest. And 5" or so for name tag. 4) I'm not at all knowledgeable in how this works, I imagine there's no set method but it seems to me it would be benificial to the art if time was taken for contemplation? I suppose that varies considerably but anyway as far as I'm concerned there's no pressing deadline, so take the time you need. 5) Again not at all sure how this works. I would prefer that the shirt back art not look like an exact delineated box with a clear between art and shirt line? I've seen shirts with art, that are transfers, but appear to have been inked right on the shirts. The art isn't "confined" it's literally outside the box. Let me know if that's possible. 6) Before moving forward with awarding the project I would like at least a rough visual presentation of 'Pegleg' if possible. OK, I'll attempt to as concisely as possible describe the project. I'll appreciate your interpretation very much Thank You and here it is:::. A tropical sundrenched island with just a small crescent of the ?sun in the top corner and a small bright white puffy cloud with a few seagulls and one mallard duck flying along with a confused look on his face. There's also a cropduster style plane with pontoons flying thru the scene that is already 60% or so off the page. There is a wooden crate dangling and swaying from a parachute aways back in the wake of the plane. The chute has 'made in Wuhan' written on it. And the wooden crate has stenciled on it 'BEANS BANDAIDS BOOZE' In hand writing and there is an x and a frowny face over the booze. The plane is towing a slightly wavy banner that reads 'dont shoot' that has a few bullet holes in it. There's also a harmless bullet hole in the planes rear tailpiece uprite. That's it for the sky. LAND) typical sandy beach with a few seashells and pieces of driftwood. A couple of somewhat (30%?) prominent palm/coconut ? trees and possibly more in the distance?to allude to a fairly sizeable island. The main focus is a grizzled rough and rugged man sitting backwards ? & slightly tilted sideways in a wooden chair on the beach next to a slightly tilted yet sturdy tall iron flagpole with a purple? flag with 'GITMO' 1st line and underneath that 'UNIVERSITY' written in pink?. He's sitting faced somewhat away( if he's sitting in the middle of a clock and you're watching him from the 12:00 he's facing 5:00) He's looking up at the slow desent of the crate wearing a long curved brim style cap backwards with a realistic eye embroidered on it. He's barefoot wearing a ? pair of over the knees hand cutoff jeans and a T-shirt with the same artwork your making now on his shirt, (enough at least to make it obviously the same?) He's holding a surfboard partially jutted into the sand with his left hand. And his left pegleg straight out and sitting comfortably on the sand. His right leg is naturally bent to the sand his foot holding a shark fin down. His right arm ends in a sharp and gleaming silver hook that has pierced the mouth end of a slightly smoking redishbrown cigar with 'CUBANA' written on it in bold black. He's got a mallard duck either standing on his left shoulder or standing/perched on the top of the surfboard? They both have comic book style talk bubbles, the duck's says "WTF Pegleg!!? no booze?" Pegleg replies "SWIM SALTY MATE".. Behind a slim coconut tree, as if he's hiding, a 'sand shark' (much like the 70's vintage SNL 'land shark') peaks his snout out and has a talk bubble that says "pizza guy?". Another just a sharkfin zigzagging through the sand towards Pegleg. Show the fins progress from the waters edge with a furow in the sand behind it. Finally the water will be gently rolling blue green waves with a small somewhat scuffed up shark that has a gouged fin and a goofy sinister look. One other, shark fin only, And that fin appearing to be chasing it's tail (much like a dog chasing it's tail) and a small section of land at the far edge of and across the water that conveys the impression of a much greater landmass and on that small land a flag just big enough to read 'FLORIDA' and/or just the iconic two circles ears and larger circle head to represent Disney World which in term reps Florida. Let me know if it's ok to have a Disney character if you know and other than that, That's it for the shirtback art and hopefully it's as descriptive as possible without overdoing it. If it appears to be to much to you, I was going by the app recommendation to list as much details as possible? Now for the shirtfront crest. It consist of six circles from 6" to 3". And a 1"wide by 6&3/4"long. This is the standardly recognized 'TOP SECRET' stamp with a thick bold black rectangular border and inside it bright bright red letters.(the red in the stamp has to sharply/starkly contrast with the dark red of the circles) The rectangular stamp crossing the circles with its bottom edge/border at the bottom of the inner 3" circle to continue across the circles left snd right to end 3/8" outside of outer 6" border on both sides. I'll begin from the inside 1) 3" very very dark (deep maroon?)♥️ red inner bullseye ? circle. Above the upper stamp line the text following the upper circle 'GUS' in bright neon ? green text The second circle 2).3&1/4" and the 1/4" in between in neon green. The third circle 3) 4" circle with the 3/4" in between in the same neon green above the line 'SWIM' and below the line 'SALTY'. The fourth circle ⭕ 4)4&1/2 the 1/2" in between the deep dark red the same as the bullseye. 5)51/4" the 3/4" between circles above the line ''GITMO U SWIMCLUB' below 'EXTREME VETTING' 6) 6" outer circle. The 3/4" in between again the same deep dark red. And centered inside this outer 3/4" red circle a white 1/2" wide x 1&1/2" long white oval at four spots.(whatever is the four centers from the stamp lines to 12:00 and 6:00. And inside each of those ovals in neon green text 'est. 2002'. That should do it for the crest. I would like your opinion on the 'stamp' as far as if it can be "stamped" off center as if by a quick hurried human hand to infer a more realistic look WITHOUT making any text in the circle illegible?? If not, can I at least turn the crest a little clockwise when it's transfered to the shirt or does that have to be decided before?? That leaves just the traditional style embroidered name tag. Maybe 3" or 4" long x 3/4" wide/ high? Make it look as if it's a white cloth patch with neon green ? stitched letters reading 'PEGLEG' on the white patch and then the patch seen on the shirt (IF POSSIBLE) Thats everything I can think to include. Hopefully it wasn't too much and too long but the app encouraged in depth details and with that said I hopefully did that. if there's questions feel free to ask.