hi,
1. Day 1, Islamabad to Kiwai, park your car, and book a jeep upto Shogran, book a hotel and enjoy.
Day 2. visit Siri Paye in morning, then drive back to Kiwai, take your car and go to Naran (night stay).
Day 3. visit straight to Babusar top, it will took 4 hours (one side) if you enjoy your ride with short breaks on beautiful places in between, came back and stay in Naran, one more suggestion you can alslo stay in Batakundi (14kilometer after Naran) for second night, as it is very scenic place and luxury hotels are available, only telenor simm works there.
Day 4. you can visit to Lalazar (it is in batakundi) by Jeep, from batakundi they will charge you 2500, came back to naran and visit Saifulmalook by Jeep, from naran they will charge you 2500 to 3500.
Day 5. you can came back to Islamabad. If you have one more day then from Abottabad you can go on Nathia Gali road and night stay there and came back to islamabad next day.
2. as far as driving skills are concerns, if you drive slow and gently you will have no problem in hilly areas, just be careful on blind turns as most public vehicles double cross on blind turns, so just use horn as precautionary measures.
in naran few places need some heart to cross water streams, i recently went naran, from naran to batakundi there is one place where upto 1300 cc cars stuck in water stream but there are persons who will pushed the car till you cross that place, hopefully till the time you visit they will clear the road, i visited on 5 june.
i've seen civic cross that place easily due to its power (1800 cc)
My suggestion is to take atleast 1000cc car. however Mehran Boss also has no issue 
3. Download offline google maps, as after naran you will not have internet, GPS will work only.
4. you can search on google you will find luxury to normal hotels, choose according to your bugget. In batakundi "Magnum Hotel" and "Regal Inn" are nice luxury hotels with 3500 to 5000 per night for 3 bed, do bargain 
5. I've shared possible trip itenarary above in point 1.