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The first order of business is to pay a visit to the authority having jurisdiction (town hall, district office, county office, whatever the case may be) and have a sit down, face to face meeting with the person in charge of planning and development. Find out what is permitted to be built. There may be restrictions on size, number of floors, proximity to property lines, roads, etc. You want to know about any unknowns that may be on record with this office, such as covenants, easements, etc. This person will be able to tell you all of the requirements for permits as well. Gather as much information as you can from this person so that you minimize the chance for any surprises down the road. Trust me, there will be surprises.

I'm nearing completion of my own house. I had to go through a rezoning approval process, which meant presenting my design to various committees as well as City council. Then there were neighborhood open houses let everyone come look at my plans. Then public hearings and votes by council. It took about a year of hard work before I got my building permit and another year of construction. It can be a very long and expensive process, so hopefully you don't have to go through rezoning. But be sure to find out what uses on the land are allowable.

As for finding a contractor, be very selective. Phone Architects who design houses in that area and ask them for recommendations. Also talk to people who have had homes built or renovated. Get recommendations and then from those, select three to interview. If you like them, then give them copies of the plans and ask for preliminary pricing complete with an itemized budget. While they are doing that, check their references. Are they licensed? Do the belong to the Better Business Bureau? Are they members of the local home builders association? Again, check their references. Talk to people who have had them do work and try to see that work. If you don't like the three you've selected, start over. A good contractor will make the whole process a little bit easier. A bad one will make life a living hell for the duration of the build and afterwards. Don't get this part wrong. Seriously. I recommend that you do go the trailer on site route. It means that you'll be there every day to make sure things are going the way you want it to.

Do you do any site supervision as part of your duties with the firm you work for? If not, I recommend you approach you boss and talk to him about adding that role to your job description. Ask to tag along with your office site supervisor for a project that is under construction, then see if they would allow you to start doing supervision work on other jobs that you are involved with as a draughtsman. This will give you a very solid understanding of how the construction process works. Information that you will be able to put to use during the construction of your own home. You'll become familiar with contracts, change orders, field review and reports, etc. You'll learn what to look for and how to correct errors and omissions. You'll learn how to deal with tradespeople and project managers. All of this is very important, as it will help you to move forward on this with confidence and competence.

The first house is tough. The learning curve is steep. But once it's done there is a great amount of satisfaction earned from seeing something you have designed through to completion. You may even decide to do another once the first is done.
 

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As for financing, I can tell you that it isn't that difficult. It may be different where you are, but I can't imagine it would be too different. You will get financing for the cost of construction after you have gone through the hoops to get you building permits, etc. The bank will want to see your drawings to determine if the amount of the loan you are requesting is in line with what the drawings show. You won't go into a regular mortgage right away. You'll get that amount as a construction loan and this will provide you with progress draws during the course of construction. The bank will establish milestones that determine when the draws can be made. An appraiser from the bank will come to inspect the home at these milestones and will determine a percentage of completion and you'll receive money from the bank that corresponds to that level of completion. During the course of the construction loan, you pay interest only until a set time period or percentage of completion. In my case, it was 9 months or 85% complete. After this, you start paying interest and principal. At the end of construction, the construction loan then converts to a standard mortgage based upon whatever rates you negotiated at the beginning of this process. The construction loan and the mortgage are actually the same loan. It just is managed closely by the bank during the course of construction and payments are interest only until it converts to the regular mortgage where you make your monthly principal and interest payments. At least that's how mine works. I would talk to your bank and ask them how it works where you are. Also, shop around for the best rates as well as the most flexibility in paying the loan down (i.e. paying it down faster).
 
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