Start by going to your county's GIS and get all the information you can about the parcel. Then research your city/county development ordinances online. Next, take your hypothetical parcel and visit your planning departments and just ask questions, you might find a person that's helpful (this may take a few visits).
Still interested? Find a civil engineer and see if one will give you the time to bend their ear and tell you what's possible. They can also ballpark costs. There's usually a job box on a build site, and in that box a set of plans by an engineer. If the development is similar to what you're interested in doing, approach the engineer on the plans.
I would also sit in on meetings - at your City Council, Planning Department, Board of Adjustments, etc. - related to subdivision projects. I've learned quite a bit just by listening to other developers push their projects through the approval process.
Like Jays said above, this is a deep pockets proposition and takes time, even on a small project. The one I'm doing - my first - has taken 2 years and two civil engineers to get through the approval process, and it's only 7 building lots. Had I not been able to self-finance the project to this point I would have been toast, carry costs on the land would have killed me before I even moved any dirt.
Here are the estimated costs on my first project: $50k in civil engineering/permitting/etc, $300k in site work (silt fencing, lot clearing, grading, retaining walls, storm water, driveways/aprons, a city spec road, a turn-round for the fire department, sewer taps, a 325' water main & hydrant..... and more.) Land cost not included.
I should have 7 lots ready to "drop a box" early next year @ a per lot cost under par for projects in the area, a number I got by asking other builders (and real estate agents) with projects near mine. That's another resource, other local builders and developers, smaller ones in my case. Most have been really helpful, and if you ask a half dozen you start to develop a consensus on best practices.
My most important lesson so far: a referral to a good civil is invaluable. Then get a referral from your civil for your surveyor. Had I started with a better civil I believe my project would have been approved much earlier.
Developing is time and intensive. Risk is high. Be prepared to be hands on 24/7/365. I am paying for an education in development, something a developer friend said would happen @ the start of my project. "You don't know what you don't know", and had I to do it over again I would have talked to as many other developers, engineers, planners, contractors, utility contractors, graders etc. as I could before I spent my first dollar on a site plan. There's a ton of knowledge out there, and most people are happy to help someone who is just starting out. In the beginning, the more curious you are the higher your chances of success. IMO.