Chris O'Brien First off, welcome to BP! David Beard Thanks for the mention.
Every region of the country has their own building requirements, and regulations that they deal with, which affects the cost of a project.
Here in California we have some of the strictest environmental standards in the country, high cost of permits, and fees for everything imaginable.
I'm sure Massachusetts is similar. In order to figure your costs, you need to find a lot that is in a location that not only zoned for the type project you want to do, it needs to be an area that is in demand, and will command the rents you need to be profitable, and produce the return you are looking for. Obviously if you can do it all with cash, that's a huge help.
Once you find the land, you need to know exactly what it is going to cost to develop the project. Are there utilities at the property? What will it take to actually hook up to them. For instance, sometimes you are charged a fee for a water meter. Many people think that fee actually means you get a water meter, when in reality, you are getting the privilege of buying a water meter and hooking up to City water. There's different things like that you have to find out.
If utilities aren't 'at' the property, how far away are they, and what will be the costs of bringing them in?
Get a list from the City that shows all of their development fees, including any school fees, park fees, etc. Find out if there are any special assessments in the area you plan to build.
Can you use a draftsperson knowledgeable on local building codes to draft your plans along with a structural engineer signing off, or do you need a licensed architect? You might look online and find some stock plans that come close to what you want to do, and take them to a draftsperson or architect and ask how much per sq. ft. do they charge to design, and make sure it's plans ready to submit, etc.
You can also use the stock plans to talk to contractors and ask them a ballpark figure for building something similar in your area.
Remember though that the plans have to fit the site, and allow for required set backs for landscaping, side yard, curb, gutter and sidewalk if required, etc.
Will you be acting as your own GC or hiring a GC and subs, or ? If you do it yourself, there's the matter of insurance, workman's comp etc. that needs to be figured out.
Sorry for the length of this post. As you can see, there is no easy pat answer for your questions. Developing real estate takes a lot of homework. By the time you see a building coming up, probably 1/2 of the work has been done.
I'd caution against trying to do a project the size you're thinking about alone on the first go round. I'd suggest you find a contractor to either hire as a GC or act as a consultant. Another idea would be to start smaller and learn the ropes. Good luck. Let me know if you have any additional questions.