Hmmm, where to start...
Ok, the first thing you need to do is forget anything you know about "CAT5" wiring, matter of fact forget CAT5 altogether. The "professionals" use CAT3 because it's easier to terminate and CAT5 is not needed.
Be sure to do a separate run from each jack location to a central location such as the basement. Be sure to use 6 position/ 4 pin USOC jacks, NOT data jacks. Terminate only the WH/BL and the WH/OR on each jack. Wrap the other two spare pairs back around the jacket.
NEVER run your jack runs out to the NID. If they ever are needed for a key system or something else they will be unuseable without major work. It is ALWAYS best to run one 4 pair (or 6 pair)out to the NID from an accessable distribution point within the house.
I don't see how a 66 or 110 block could be applicable, into tying 3 runs into 1 line.
Your problem is your computer background/network wiring experience is a handicap. A 66 block IS the way to go, matter of fact use two, they're cheap (mounted with 89 brackets please.) Use one split block (50 pair) to punch down all 4 pairs of all your runs. You can do 6 runs down the left side. Use bridging clips to join the halves. Mount another split 66 block to the right of it. The CO lines from the NID run (4 or 6 pairs) get punched down starting on the top left. Bridging clips again (you only need to do the first two rows if you only use 1 line).
Now with cross connect wire come off the right side of the CO block line 1 (WH/BLs) and daisy chain all the WH/BLs on the right side of the premises wiring block.
The reason for this is twofold- maximum flexibility if more lines are added or a key system is installed and it provides a means to isolate individual jack runs or a CO line for troubleshooting without disconnecting wiring.
-Hal
