The home is in our names and we have a loose organizational system that consists of receipts/bills in a bill planner (combined with those of our primary residence) and some files in a filing cabinet.

This just involves being a planner and planning for the crap to hit the fan.  

What I'd do is walk into Building and Planning with the parcel or listing sheet and meet with a planner.

Speak with one of the planners and find out what is allowable and what permits costs and get a pulse for what they are currently have allowed other sites in the area.

My name is Wes Pittman and I'm a transportation planner by trade with a masters degree in urban planning. 

I am a former City Planner in training and practice.

Remember when you buy you're really locked there cause you'll have to pay Realtor commissions when you go to sell, there really isn't an easy out without taking a financial hit unless you can rehab and flip.Make a tight budget and talk to a financial planner. 

You could partially convert over several years.I suggest talking with several people, including accountants and perhaps a financial planner (not a product pusher), on this decision.I knew a woman who had a sizable balance in her IRA and converted ALL of it to a Roth in one year so she could spread the tax payments over 5 years (the rules back then).  

Financial planners who understand realtors would be a great niche. 

Its not something most folks just try to do on their own. but if this is a small project and you want to learn it seems like its small money.. buy the dirt for 60k and go talk with a land planner and civil engineer.. get pre app meetings with whatever government agency in the jurisdiction controls land division.. it can be a good learning experience for you.. and being this is such a small amount of money it could be good practice and one to get started on.. don't do it though if you can't afford to lose the money.I usually lose between 30 to 50k a year doing preliminary work on subdivisions that I end up not buying because you just don't know all the facts until you spend some money trying to engineer them and go through the process.