I've long thought this was a brilliant idea and something I could see HHH doing once he has complete control. In my mind WWE leaves money on the table. When some states are only run once a year, places that supported territories on a weekly/monthly basis, there is money out there providing there are resources to support it (indies don't have those resources). Keep in mind, most territories died because WWE killed them, not because they were not self-sufficient. Talent raids, predatory business practices (snaking TV and arena deals) killed the territory system. Now I don't think any new territory would ever grow to their previous incarnations success, but I think they could be completely self-sufficient over time and provide the unique feeder system that ultimately created the 80's and 90's boom.
I think there are a few key factors that would need to happen for it to accomplish something more than the current developmental system, which I would alter to make a combination school for new talent and graduate school before a guy moves up to the roster, so here's how I would set it up:
1) You contact guys guys with a background or mind for booking. Whether it's Jim Cornette, Kevin Sullivan, Dutch Mantell (once his run is finished of course), Jake Roberts, Kevin Nash, Scott Hall, Jim Ross, Shawn Michaels, etc. and you propose a partnership. They will receive a downside guarantee and whatever money the promotion makes beyond that is theirs. They need complete creative control (that means if they want a few vets with no future, then that's their call) and the incentive to draw money using the talent they can find, whoever those wrestlers are. Let them be your scouts and talent development, with the intent of teaching guys to draw money however they see fit with no WWE interference. You initially agree to pay 14-20 wrestlers for each promotion at indie market value in guaranteed contracts (only at the start) that favor the territory, which means they can be fired.
2) WWE agrees to be a silent partner. They will provide a non-refundable investment to get started, a business manager to handle TV/Arena/etc, an accountant to manage the books/payoffs, a grassroots advertising/marketing guy (this could be an intern position staffed through local colleges) and trademarks where applicable (which WWE retains ownership of) and the agreement that WWE is never associated with the new promotions in any public advertisements or acknowledgments. This provides accountability to WWE and the assurance the territory will not be associated with WWE, negatively or positively. If possible, you might even look for investors/business partners for each territory from pre-existing business relationships. Essentially you want to set it up like the old territories, where the booker and investor own points in the office, while WWE keeps both a stake (dividend payments when the territory succeeds), control of trademarks, and access to talent.
3) You look at your numbers and see which parts of the country are your strongest states/regions/TV markets. Which places draw the best ratings and attendance, where do you ship the most merchandise, etc. Those will be where you avoid placing a new territory, instead focusing on markets where theoretically there exists a good/historical wrestling market not penetrated by WWE where new stars could develop and bring that audience to WWE when they move up (think Hogan taking the AWA fans to WWE). You run small venues, focusing on smaller cities that WWE does not visit, trying to keep the driving trips manageable withing an initial TV market, then trying to expand as business dictates.
4) You match your strongest trademarks as close to their historical strongholds as you can or you simply create new ones and you place bookers as close to their current homes as possible, where they may enjoy local fame/connections and keeps relocation costs down. Then WWE puts together a sales crew who will help open the booking office, arrange small venue deals, and identify local TV affiliates to get each territory TV with which to promote and agree to send 2-4 WWE Superstars to help get the show off the ground. After which, the Booker, business manager, accountant, and interns will run the territory and can only add staff as they can afford. If they grow, they grow.
5) You agree that you have right of first refusal on talent who agree to work in the territories, along with the promise that any talent you do take will give the territories a one month notice and WWE will provide a fresh investment to compensate for the territories loss, whether that's cash or a WWE superstar reassigned.
6) The territories will take 30 days off in the month before WWE visits a market for Raw/Smackdown. This will protect WWE's market strength and the new territories can plan around this each year or potentially work a co-promotion where the territory guys work locally advertised dark matches, either against each other or in angle with current WWE superstars who are sent down in the previous month to set it up on TV. Business can dictate this.
7) A talent share/send agreement. You not only want to take new talent, but you want to send it a well. Whether it's a new trainee or even a WWE guy who needs to be refreshed or repackaged. So when a Zack Ryder is about to be future endeavored, WWE can offer him a spot in the territories, with the promise he can leave whenever he wants providing WWE gets right of first refusal (should TNA come calling) and he gives 30 days notice.
8) An office intern agreement. WWE can use their corporate stature within academia to provide the territory access to free/cheap college interns for college credit in positions that could lead to a position in WWE. Aspiring writers, producers, cameramen, directors, etc can also gain unique on the job training that could benefit WWE down the line.
That's how I'd do it anyway...