Understand that this is not going to be a quick process.
First, you'll have to file your suit in court. Most likely, you will not be given a court date at the time you file the suit. A court date will be set after the defendant (and his attorney, if he has one) has been notified. The court date will be for some future date, but even once you've been given a court date it may change. The court date can change at either the discretion of the court or the reasonable request of either party.
At the hearing for your suit, you may or may not be notified of the decision of the judge (most likely not). The judge will consider the arguments of both sides and render his decision at a future date - typically within a day or two. You will then be notified by mail of the decision. Assuming you win, the defendant will have a period of time to appeal, during which no action can be taken against him. The appeal period varies but is likely on the order of 30 days. After the appeal period lapses, any collection action can begin. It is also likely that you will have to initiate the collection action. What actions are available varies widely, so you'd have to discuss this with the court.
Even if the judge finds in your favor, it doesn't mean that he will find for the amount you are seeking. The judge has discretion in the amount of the award. If he feels that some arguments made by the defendant are valid, he could award you an amount less than what you are seeking.
Maybe so. However, you will be at a very serious disadvantage if the defendant hires an attorney. The legal system is built on a complicated system of rules and procedures. Your case could easily be dismissed simply for failing to follow the smallest procedural detail (filing the wrong form, filling out a form incorrectly or incompletely, filing a form with too few copies, and all sorts of minutiae). In fact, a procedural fault could result in your case being dismissed before it even gets to trial. Lawyers love these little detailsAnd the way I see it, this contractor has clearly wronged me, and I alone can prove beyond a reasonable doubt that this person has wronged me.
Also, be sure to check, in advance, of all court costs, filing fees and related expenses. There may be costs/fees to execute on a judgment that are in addition to the court costs. Also check if any of these can be added to the judgment. If you cannot recoup these fees from the defendant (there are jurisdictions where you cannot) then these will be your responsibility and will effectively reduce the amount of the judgment you receive.
Again, I'm sorry to say, but I find the idea of traveling half way across the country, incurring significant out-of-pocket travel expenses and court costs, the possibility of multiple trips, and waiting months to potentially receive a judgment in some amount, to be a dubious effort for $1000. I understand the loss of potential income of $1000, but you will put in a good bit of time, effort and expense in chasing it - probably considerably more than you now realize.