Albert J. Harnois III
I'd personally go for the Blackmagic Pocket Cinema Camera with some Super-16 glass. It actually has a bit more dynamic range than the D-16, so you can get a bit more information from the highlights. There's a guy on Vimeo that uses this combo and get's great results: https://vimeo.com/76197137
He also used this Kodak 2393 LUT which gives a nice retro brown look. Reminds me of "Hannah and Her Sisters" or "Margot at the Wedding". The LUT can be found here: https://vimeo.com/57785040
For diffusion I'd go with the 1/4 and 1/8 Black Pro Mist filters from Tiffen. Sean Price Williams used them on his film "Christmas, Again". You can see them in action here: https://vimeo.com/147614395
Here's a link to the ASC article with Sean talking about his lighting process on that film: https://www.theasc.com/ac_magazine/February2015/Sundance2015/page3.php
And BTS footage from "Listen Up Phillip": https://vimeo.com/124527554
He learned that trick from Robert Altman. You put a zoom lens on a dolly, track in, and towards the end of the shot zoom in. The dolly move helps cover up the zoom and allows you to quickly move from a wide to a close-up without the use of a cut, lending a sense of momentum or propulsion to the shot.
18mm or 20mm - wide angle
24mm - medium
28mm or 35mm - normal
50mm - moderate portrait, mild telephoto
85mm - portrait, telephoto
Sort of. He's using a 50mm in Academy, which has an aspect ratio of 1.37:1. If you were to use a 50mm on a full frame camera and crop the sides you'd get the same look. So yeah, in a way I guess you could think of it as a full frame equivalent.
Get the Nikon D5500. There's none of the moiré or aliasing you'd get with the Canons; it's sharp, so no 'mushy' footage. It shoots at 60fps in 1080p, unlike the Canons, so you can get real slow motion in full HD. The Sigma 17-50mm f/2.8 is an awesome lens, it's perfect for a budding filmmaker. I'd look into the Shure LensHopper for a microphone; it has a built in digital recorder and a headphone jack, so you can monitor as you record. All three can be had off ebay for 1,100 bucks. You can get an AmazonBasics camera bag for 40 bucks. That leaves 360 bucks for a tripod and fluid head; a Manfrotto tripod and head typically go for 350 on ebay, so you should be good with the 1,500 budget. Good Luck!
There's a children's game called Bigger and Better. A person trades a small item(paperclip) for a larger one(a pen), and works their way up the bartering ladder until they get what they want(a car). With all the trades there would be a whole lotta handshaking going on. This idea has been done to death by sitcoms, but it's still a viable option. Here's a classic example from "The Office" http://economicsoftheoffice.com/all/?eps=7_19
Then of course there's the protagonist who wants to make a good impression on his boss, or prospective father-in-law. He stresses about the first handshake: technique, grip, humidity(sweat), duration. He's having fever dreams of failed handshakes. Have it build up and up, until the moment he finally goes in for the shake and the boss/father compliments him on his technique and remarks how he has such a masculine grip. Then as the tension recedes, the protagonist in a fit of relief smiles, retracts his hand and let's out a 3rd grade schoolgirl giggle to end all giggles. Cut to a look of dread on everybody's face.
Anyways, whatever you choose to do it sounds like an intriguing concept for a project and I'd be interested to see what you come up for it. Good Luck!