Main story missions -> Set it up in 2 columns and break it up in chapters like they did on gta4.net. It would just make it an easier layout to follow.
Little Jacobs drug deliveries -> list the delivery locations and check each one off.
Festival Towers Meadows Park
Cerveza Heights Car Stack
East Island City Delivery
Meadow Hills #2
Outlook Park Delivery
Brucie's Exotic Export -> Same thing as Jacob
-Random Order too I think-
Brucie's Races -> Split them into 3 groups based on their location:
(I had to be in their respective zone in order for Brucie to let me race them)
Broker-------------| Algonquin----------| Alderney
South Broker------| South Algonquin--| North Alderney
Airport Run--------| Star Junction------| Elevated
Dukes Boulevard-| Road to Bohan-----| South Alderney
Stevie's Text Message Cars -> Break it down into 2 or 3 columns
Most Wanted -> Split into 3 columns
Friend Activities -> Split into 3 columns. One column per friend. Also note that "Little Jacob" doesn't cross out and become gray, while brucie and packie does. (Atleast it doesn't on my screen).
Random Pedestrians -> Put a check box for each meet. Also link "Random Pedestrians" to the Random Pedestrians page, and link each name/meet to their respective pictures.
Flying Rats -> Put a check box for each one, and link the "Flying Rats" title to the flying rats page, and link each # to their respective picture. This will help people find missed ones easier. 2.5% / 200 rats = 0.0125% per rat.
Unique Jumps -> Same thing. Check box for each one, link "Unique Jumps" title to the unique jumps page, and link each check # to their respective picture. Same thing for helping people find them easier. 2.5% / 50 jumps = 0.05% per jump.
This will make these 2 sections a little bit longer, but if you compress the other ones mentioned, and put 5-10 check boxes in 1 row for the rats & jumps, it would equal itself out.