I've completed 87% of the project with just 12 road trips and three other minor outings:

Boston, June 1999
Capitols this trip: 3. Total: 3.
Signs this trip: 4. Total: 4.
The Project is born in Boston!
IN: Drive south on I-93, I-95, and US-1A through Massachusetts to Pawtucket Rhode Island. Continued into Providence. West on US-6 into Connecticut. Continue on US-6 and CT-195 to Storrs, west on I-84 to Hartford. Down I-91, west on I-95 and I-287 in New York. Drove around the Suffern area looking for a New Jersey sign, but didn't find any.

Hall of Fame Weekend, July 1999
Capitols this trip: 1. Total: 4.
Signs this trip: 0. Total: 4.
OUT: From Shea Stadium, west on I-495 to Van Dam Street and the Queensboro Bridge. North on FDR Drive to the George Washington Bridge. I-80 west to NJ-17 north to I-87 north into Albany. West on I-90, I-88, US-20 to NY-28 south into Cooperstown.
IN: NY-28 south to I-88 west to NY-206 south to NY-17. NY-17 south to I-87 to I-287 home.
Winnipeg Business Trip, August 1999
Capitols this trip: 1. Total: 5.
Signs this trip: 0. Total: 4.
Met my college roommate during a layover in Minneapolis. My connecting flight was delayed a few hours so we went to dinner and then stopped in St. Paul.

Washington DC, October 1999
Capitols this trip: 3. Total: 8.
Signs this trip: 4. Total: 8.
OUT:West on I-78 into Pennsylvania. Stopped at Roadside America. I-78 ends at I-81. South on I-81 to Harrisburg. Continue on I-81 south into Maryland and West Virginia. Visited Harpers Ferry, and then drove to the Virginia-West Virginia line. MD-17 north to I-70 to I-270 to Washington.
IN:Left D.C. east on US-50 to Annapolis.
Continued on US-50 to the Maryland Eastern Shore. MD-302 to the Delaware line.
DE-11 to DE-8 east towards Dover. North on DE-1 and US-13 to I-95 into Philadelphia,
US-1 home.
Driving Around, November 1999
Capitols this trip: 0. Total: 8.
Signs this trip: 1. Total: 9.
Finally found the New Jersey welcome sign ("the", not "a", or at least it seems that way) on I-95 about eight miles from the actual state line.

Y2K in the White Mountains, December 1999-January 2000
Capitols this trip: 3. Total: 11.
Signs this trip: 3. Total: 12.
OUT:I-95 to I-91 to I-84 to I-90 to Boston. North on I-93 into New Hampshire. Continued north on I-93 into Concord. North on I-93 to NH-115 to NH-16 to the campsite.
East on US-2 into Maine. East on US-2 to ME-26 to US-202 into Augusta. South on I-95 back to Boston. Two days later, north on I-95 to NH-16 back to the campsite.
IN:New Year's Day. West on US-2 into Montpelier.
South on I-91 to I-89 to the Vermont-New Hampshire line. I-89 to I-93 back to Boston,
and then back home.
Driving Around, April 2000
Capitols this trip: 1. Total: 12.
Signs this trip: 0. Total: 12.
Took a trip to Zinn's Diner in Lancaster County, Pennsylvania. Along the way stopped in Trenton.

Cincinnati, May 2000
Capitols this trip: 3. Total: 15.
Signs this trip: 3. Total: 15.
OUT:I-78 west into Pennsylvania. I-81 south past Harrisburg and into Maryland. West on I-70 along the Maryland panhandle and I-68 into West Virginia to Morgantown. South on I-79 into Charleston. West on I-64 into Kentucky. Visited Frankfort. North on I-75 into Cincinnati. Walked across the bridge into Covington, Kentucky.
IN:West on I-74 to the Ohio-Indiana line. (Should have gone to Indianapolis.) North on I-71 into Columbus. East on I-70 across the West Virginia panhandle into Pennsylvania. I-76 to I-81 to I-78 home.
Dallas, December 2000
Capitols this trip: 12. Total: 27.
Signs this trip: 14. Total: 29.

OUT: Day One: South on US-130 to US-322, across the Commodore Barry Bridge, and into Pennsylvania. South on I-95 into Delaware. Retook the Maryland sign picture. I-95 south to Baltimore, then south on the Baltimore-Washington Parkway into D.C. I-95 south to Richmond. I-64 west to I-81 south to Bristol VA.
Day Two: I-81 across the border into Tennessee. I-81 to I-40 west. Past Knoxville into Nashville. West on I-40 to Jackson, and US-412 north to I-155 into the southeastern corner of Missouri. South on I-55 into Arkansas. I-55 to West Memphis, and the I-40 west to East Little Rock.
Day Three: I-630 into downtown Little Rock. I-40 west into Oklahoma. Muskogee Turnpike to US-69 to Vinita. OK-2 up to the Kansas line and back. West on I-44 to Oklahoma City.
Day Four: I-40 east to US-177 south to OK-3B into Ada. OK-1 to I-35 south into Texas. I-35 into Dallas.
IN: Day One: I-35 south to Austin.
TX-71 east to I-10. I-10 east past Houston and Beaumont into Louisiana.
Day Two: Visited Baton Rouge. LA-37 north to I-55 to the Mississippi-Louisiana line. North on I-55 into Jackson. East on I-20 to the Alabama line. US-80 east into Montgomery. US-231 south into Florida.
Day Three: Visited Tallahassee. US-319 north to the Georgia-Florida line. North on I-75 past Macon where I broke down (wheel bearing failed, ruining a rotor). I-75 north into Atlanta. East on I-20 to Augusta.
Day Four: I-20 east in to South Carolina, then turned around and went back to Georgia. Then turned around again and went back into South Carolina. I-20 east to Columbia. I-20 east to Florence, and I-95 north into North Carolina (and South of the Border). Turned around and back to get a South Carolina sign. I-95 north to I-40 west into Raleigh. US-64 to I-95 into Virginia. US-58 east into Norfolk. US-13 north on the Chesapeake Bay Bridge Tunnel onto Virginia's eastern shore and north into Maryland's eastern shore and Delaware. I-95 into Pennsylvania and US-1 north into New Jersey and on home.
Kansas City Business Trip, June 2001

Capitols this trip: 2. Total: 29.
Signs this trip: 2. Total: 31.
I-70 east into Kansas to Topeka. North on US-75 into Nebraska. West on NE-2 into Lincoln. East on NE-2 into Iowa. South on I-29 to I-35 back to Kansas City. Looking back, I should have gone west from Topeka to Manhattan and then north on US-77 to avoid repeating NE-2. Oh well.
Mesa AZ Business Trip, January 2002
Capitols this trip: 1. Total: 30.
Signs this trip: 2. Total: 33.
Pretty simple. Sky Harbor Airport to downtown Phoenix. I-10 west to the California-Arizona line and back before I even checked into my hotel. I was toying with different trips, such as to Nevada or Four Corners or Santa Fe, but I wouldn't be spending the weekend.
Beaverton OR Business Trip, April 2002

Capitols this trip: 2. Total: 32.
Signs this trip: 2. Total: 35.
Several different excursions here:
- I-5 south from the Portland area to Salem and back.
- I-5 north into Washington up to Olympia and on to Seattle and back.
- Also went to Mt. St. Helens, across to Oregon at Longview, Washington, and west on US-30 to Astoria. Across the Columbia into Washington.
- East on I-84 along the Columbia River Gorge to Hood River and Cascade Locks. Crossed the Bridge of the Gods into Washington and back into Oregon.

Lake Erie Circumnavigation, August 2003
Capitols this trip: 1. Total: 33.
Signs this trip: 1. Total: 36.
Day One Leave a wedding reception in East Windsor, New Jersey. CR-571 to US-206 north to I-80. East on I-80 into Stroudsburg, Pennsylvania. Spend the night at a friend's house.
Day Two I-80 west into Ohio. Merge onto the Ohio Turnpike. I-77 north into Cleveland.
Day Five OH-2 west into Toledo. I-475 west to I-75 south to US-20 west. Turn right on OH-109 north into Michigan. OH-109 becomes M-52. M-52 north to US-223. North on US-127 into Lansing. East on I-96 into Detroit.
Day Seven East on I-94 to Port Huron. Cross into Canada. East on ON-402 into London, then merge onto ON-401 east to Toronto.
Day Nine West on the Gardiner Expressway to Queen Elizabeth Way. QEW east to Fort Erie. Stop at duty free and cross the Peace Bridge into the United States of America. South on I-190 through Buffalo, and then west on I-90 for one exit. East on NY-400 to US-20A. Go east on US-20A past Warsaw, then south on NY-36 to Mt. Morris. South on I-390 to I-86/NY-17 to Binghamton. I-81 south into Pennsylvania until Scranton. East on I-84 and then south on I-380. Get stuck in Sunday night traffic so bail out on PA-715 to PA-611 back into Stroudsburg, hang out there for a while. I-80 east into New Jersey, then US-46 east to NJ-31 south into Clinton. I-78 east to I-287 south to home.

St. Louis, September 2005
Capitols this trip: 3. Total: 36.
Signs this trip: 1. Total: 37.
Day One Leave home to crash at a Vanya's house in Allentown, Pennsylvania. I-287 north to I-78 west to US-22 west.
Day Two I-78 west. Get stuck for almost an hour at Exit 19 because a truck had spilled something onto the highway. Merge onto I-81 down to Carlisle and then pick up the Pennsylvania Turnpike. Stay on I-70 into West Virginia, Ohio, and Indiana. Stop at Greenfield, Indiana.
Day Three I-70 west into Indianapolis. I-74 west into Illinois. I-57 south for one exit and then I-72 west into Springfield. I-55 south into St. Louis.
Day Four Day trip: I-70 west to US-54 west into Jefferson City and back.
Day Six I-70 from St. Louis all the way to Breezewood, Pennsylvania. Pull into Breezewood about 12:30 am. All the motels were full so I decided to just go home. I-76 to Carlisle, I-81 north to I-78 east to I-287 home, arriving at 4:27 am.
Big Bear Lake, August 2008
Capitols this trip: 7. Total: 43.
Signs this trip: 7. Total: 44.

OUT: Day One: I-287 north to US-206 north to I-80 into Pennsylvania and Ohio. OH-225 and US-62 into Canton. US-30, OH-598, and OH-309 to Marion.
Day Two: OH-4, US-36, and US-68 to I-70 into Indiana, Illinois, Missouri, and Kansas. Stop in Topeka.
Day Three: I-70 through Kansas with a pit stop in Manhattan. Visited Abilene. US-81 north to K-191 to the geographic center of the contiguous U.S. north of Lebanon. US-36 west into Colorado. CR-217 to a pit stop in Deer Trail, and then I-70 west into Denver.
Day Four: Visited Denver. I-25 south into New Mexico and Santa Fe. I-25 to I-40 west to East Gallup.
Day Five: I-40 west into Arizona and California. CA-247 and CA-18 into Big Bear Lake.

IN: Day One: CA-18 to CA-247 to I-15 into Nevada. I should have stopped for the sign, but I didn't. I-15 north into Arizona and Utah. I should have stopped for the sign, but I didn't. I-15 north to Nephi.
Day Two: I-15 north to Salt Lake City. I-80 west to Wyoming. I couldn't stop for the sign here, so I take WY-89 up about 12 miles each way to the Utah-Wyoming border for a two-fer. I-80 east to Cheyenne.
Day Three: Visited Cheyenne. I-25 north to US-18 and US-85 to Newcastle. US-16 east into South Dakota. US-16 to SD-244 to Mount Rushmore. SD-244 to US-16A to US-16 to I-90. I-90 east to Wall Drug. US-14 east into Pierre, where I am right now.
Day Four: Visited Pierre. US-83 south to I-90 east. Visited the Corn Palace. I-90 east into Minnesota. I-90 west back into South Dakota to I-229 south. I-29 south into Iowa. I-29 south to I-680 east to I-80 east to Des Moines. I-80 east to West Branch.
Day Five: I-80 west to IA-1 to US-151 to IA-136 into Dyersville. County Road D17 into Dubuque. US-151 into Wisconsin to Madison. I-39 south/I-90 east into Illinois. Double-back into Wisconsin. I-90 east through Chicago to I-94 east into Indiana. US-20 to OH-2 to US-31, shunpiking the western two-thirds of the Indiana Toll Road. US-33 into Elkhart.
Day Six: I-80/90 east into Ohio. US-6 west into Fremont. US-6 east to OH-2 east to I-90 east into Cleveland. I-480 to US-422 to OH-82 to OH-7 to the Youngstown area, shunpiking the eastern two-thirds of the Ohio Turnpike. I-80 east into Pennsylvania. PA-33 to I-78 into New Jersey. I-287 home.