My ordering is roughly similar to Bickendan's. It's based largely on when route systems were added to CHM (which started with Interstates, then expanded into US routes and other systems) and TM.
Same here.
CHM had interstates first, so I've listed those first. 3dIs follow their parent 2dIs.
Then, Business Interstates.
Then, US Highways, with bannered routes mixed in following their parents.
These groups are sorted alphabetically by state postal abbreviation.
Next come the state systems, sorted again by postal abbreviation for the corresponding state.
These are sorted by
system, so
ME NH113B is in with a bunch of NH routes, and
NH ME153 is in with a bunch of ME routes.
USASF are sorted by state, lumped in with the state routes.
When the provincial routes in the Maritimes were activated, I added everything to the end of my .list as one big road trip, listing all the segments in the order and direction in which they were traveled. (I've only been there once, when I was 8 or 9, and my .list file here is a best guess.)
Since then, three "major" road trips since late 2013 have been added at the .list's end. Otherwise, one small clinch here or mileage extension there gets sorted with the other stuff from its tier & state up in the main body of the list.
I often need to do a Wordpad search within my list file to find ... where to add new entries.
Ayuh. I search for
ME ME, then hit Page Down however many times.
One other thing I do is try to group together entries for a route within a state, in order of where they show up in the Highway Browser. That makes it easier for me to fold entries together when I fill the gaps between them.
Same here.
I've sorted State route segments by route number/name; disconnected segments of the same route go in 'HB order".
The one exception is Vermont State Highways. A relative latecomer activated only after CHM was superseded by TM, VT got sorted at the end of the state routes section (alphabetically after RI) & before the Canadian Maritimes. Vermont State Highways themselves are sorted into several individual mini-roadtrips in Vermont over the years.
For the list lines themselves, I enter them in the direction traveled:
State Route Begin End.
So if I travel
ME I-995 1 4 and then
ME I-995 6 3 and these would overlap to form a single .list line, I'd probably just list them in the order in the HB,
ME I-995 1 6.
There may be some overlapping or redundant lines with the sections where I've listed individual trips, but I'm not too fussed about tidying them up muy pronto.
Also, I try to remove or avoid adding list file entries that are entirely concurrent with other routes (in early CHM days, we needed such duplicate entries, but now automatic multiplex detection makes them unnecessary). For example, many Texas Interstates are concurrent with U.S. routes, so I just list the U.S. routes without duplicate entries for the Interstates.
I avoid adding these now, and will trim out unnecessary ones when I come across them, but doing so is not a priority. (When NY343 was relocated recently, I just deleted its entry from my .list, as all I had was the NY22 concurrency.)
Thus I have no Future Interstates .listed, as
NY17 is sufficient.
No TCH in NB or NS, just listing NB2, NB16, NS104 & NS106 instead. I do have some
PE TCHPEI listed. This tells me I added this stuff to my .list before the PEI provincial routes were activated. Holy wow. No other PE roads are listed; I'll have to figure out where I went again, and see if there's anything more I can add...