A 600cc sportbike is NOT a middleweight bike. It may sound middleweight compared to the liter bikes and the 'Busa/ZX-12R/Blackbird, but displacement does not equal tameness. Even an early 90s 600cc sportbike puts down 80+hp at the rear wheel. On my FZR600, that is equal to ~400hp at the wheels in a typical sports car. They are nervous, twitchy sensitive machines and they are not good things to learn on. It only gets worse as the bike gets newer.
It is very easy to sell a 250-500cc machine. Very easy. I sold my Ninja 250R in four hours. A smaller bike will teach you all the basics and allow you to push limits safely. More importantly, they won't hurt you as badly (depending on how you screw up) as a 600 will. They can keep up with anything out there except in the straights and that doesn't matter anyway.
You need to learn to crawl before you can walk. You don't learn to swim by saying the shallow end is for pussies and just jump into the deep end and expect to learn by thrashing around. People will drown if they do that. Learning to ride well is a process and it is best taken in steps. You're 19, you have years and years ahead to upgrade and step through various bikes.
Saying you are just going to upgrade anyway so you might as well get the dream bike is weak. It's weak because everyone upgrades. Almost no one keeps the first bike for long. Why? Because until you've spent time in the saddle, you honestly have no clue about the type of riding you will do and the type of bike you really want to ride. After a year or two on a starter bike, you have the experience and perspective to look more critically at that second bike and get one that truly matches your riding style, desires and needs. I'm still not there yet with my second bike. My third bike will be the one that really fits me right.
On gear, do not ignore pants and boots. Lower leg and ankle injuries are quite common and proper riding pants and boots go a long way towards preventing or eliminating it. Jeans and work boots are not protective gear. I'm biased on gear. I value my skin highly so I don't cheap out on gear. The cheapest item I own are my gloves. My cheapest jacket is my hot weather at $200. I trust it for in-city and light highway use. I prefer leather and always wear leather pants and good riding boots no matter the weather conditions or temperature. The rule with gear is examine it and then imagine yourself sliding along the pavement in it and decide if you will be comfortable doing that in it. Before buying any gear, search for first-hand accounts of riders going down in what you are considering. I don't care what the companies say. I look for what riders say. Or racers. If a racer falls in it and gets up, it heads to the top of the list.
Does your budget include maintenance? As the bike gets bigger, so do the costs. Especially in tires, chains, sprockets and plastic. Unless you plan to do all your own maintenance, you need to factor in routine maintenance. Bikes are very demanding in that arena. I might slide on my car but I am religious on bike maintenance. A minor problem might get my car in the shop. Ignore something that needs to be done on the bike and it can kill me.
$120/month for insurance is insane. You might get away with it on a 600 depending on the insurer. A 250/500 will likely be several fold cheaper and you can probably get better coverage. Remember, even though a Ninja 250/500 or a GS500 might look (and act) like a sportbike, many insurance companies consider them standards. That gets them out of the sportbike (and high risk/high loss) classification. There is a reason why 18-25 year olds have the highest insurance rates out there on sportbikes.
I recommend David Hough's "Proficient Motorcycling" series for starters. There are two books. The first is essential reading. The second is better appreciated after you've been riding awhile.
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