Whenever I open up a new project, I take full stock of the situation and of perceived needs in each department. I often take 3 to 5 weeks to build a proper vision of what needs to be done. I found that complete emptying, washing
of the boat IN PERSON works best - I mean go to the top of the mast
but also clean the bilges ... yes. Start every system, run every piece of equipment
. Time consuming, yes, but lets you know the boat intimately which speeds all up work later on.
As I go thru the boat and her systems, I daily dump this virtual salad into a spreadsheet (actually, I no longer use Excel as there are so many decent free options, starting with OpenOffice, King suite, Libre O suite, etc etc). I keep a small booklet, a camera
and a pen on me at all times. I fill them up daily, as I go. I take down everything. Everything.
Now with this very raw and general picture in my spreadsheet, I split the jobs into groups as per each boat department, and I keep track of the department in the right column, then envisioned time frame in the next column, then the pro forma budget
in the next column, and so on.
I make a copy of this spreadsheet on another computer. Just in case. I back up later, on a regular basis (weekly, unless I take a week off).
Then whenever I need the time-frame view or the budget
view, etc. I simply sort the table by respective column.
I expand and extend the table as I go deeper and deeper thru the project. I also generate views for all contractors, the owner, etc. as necessary. I never remove the "done" items (a common mistake with project greenhorns) - I mark them gray and keep them in the table.
One thing I have learned the hard way: making a great vision-plan is one thing, following up and keeping track is another art, possibly equally important for less stress on the job and for better progress (as well as lower budget ...). Take notes, keep bills, review them, REGULARLY.
I also make regular (weekly and monthly) reports, also when such reports are not required by the owner. These reports somehow help me clarify the vision of what has been achieved and what is coming up next.
The above is roughly how I work on big boats, where projects tend to last 6 months to 3 years.
Now on our own boat (that is only 8 meters long) ... I just make a handwritten list of jobs, split them into dry (boatyard) and wet (marina) jobs and then I go at them and do as many as I can before we depart. Last time I started with about 100 items and went down to about 30 (with maybe another 100 items that rolled thru the list). That was 6 months of pseudo work, OK 3 months of so-so work, OK 1 month of hard day to day work.
Sure thing, if you are already into any specific project management software, then the choice is obvious. But if you are not using one every day, then you can just make do with a spreadsheet and a notebook.