Salam
We visited Skardu last year. We started the tour on 26th of June and got back by 2 July. We were 8 friends and travelled from Lahore on two vehicles (a Ciaz and a civic 7th gen). We spent around 90k on petrol and fuel was around 237 i think.
answers to your questions
1 & 2) It is advisable to break the journey into two parts. Naran is a very good stopover and so you should ideally reach Naran by evening of the day you intend to start your travel. It is better to set off as early as possible (3-4 am). This is the case if you are taking the Babusartop route. If you plan on taking the KKH route then Besham is usually the place where you can spend the night. It has a number of good hotels and you will be easily able to reach there before nightfall. I have never used KKH for my travels to GB but I have heard that it has improved a lot with very little broken patches so should be good. On day two you will either start from Naran or Besham and will be able to reach Skardu before nightfall. The Skardu morr is the start of JSR ( Jaglot Skardu Road) and it is a pleasure to drive on! You travel along the Indus river and it is around 180 kilometers from Jaglot to Skardu. Half way there is a nice place called Astak Nala which is famous for its nice meals. If you dont stop then it will take you around 3-4 hours depending on your speed. The JSR did have land sliding at a couple of places when we went and honestly in case of land sliding it can be a bit tricky since it takes a day or two for FWO to clear them up. We fortunately got a very good window during which the roads got cleared just as we reached the area. So its a good idea to follow local district admin on twitter to get updates on road situation.
3) You will reach Skardu by evening of day two and it has plenty of accommodation options. Make a list of hotels by looking at online reviews and then its a good idea to go there and negotiate the rent. This was feasible for us since we were a bunch of friends. But with family it can be a bit problematic so you can make prior bookings. Skardu has plenty of hotels and also guesthouses and is a very safe city. Dont expect food to be extravagant since Skardu is not famous for its food. Buy SCOM sim as you reach there and it gives okish internet coverage.
4) Katpana, Sarfranga, kachura (upper is freely accessible while lower Kachura is part of Shangrilla resort and has 1000 Rs entry fee) , shigar, mantokha, khaplu, Deosia and lastly Bashu Valley !!!! you wont regret it!!! visit them in this series. For Bashu you will have to park your cars along the river indus and hire a jeep. It is a one hour jeep trail which is very steep at some places but trust me once you reach that place it is extremely beautiful and peaceful. Hotels are available there with camping areas as well with full arrangements.
5) You will need the jeeps only for Deosai and Bashoo. Rest of the areas you can cover on your cars. Skardu itself is not that amazing and the weather shall be hot during the day and cool during the night. Make sure you travel on prados only and dont fall for older FJ-40s as their rent is cheaper (you will thank me later). Rents vary between 15k-20k/day for prados and land cruisers + diesel.
Expect open air bathrooms at places like Deosai and Bashuu. They will be cordoned off but mostly without roofs. When you travel to Deosai then leave early and take jackets with you. You will not need them during the day but at night it gets very cold. There are camping arrangements at KalaPani and even at Sheosar lake.
Do let me know if you have any other questions...remember Skardu itself is not really that much of an attraction but areas around it are.