From reading your post it sounds like you are just starting the learning process. Before I ordered my first kit in February I spent about a month doing nothing but researching and watching videos on youtube.
In the end, I ended up buying this kGo kit:
KGO kit1100mAh by SLB
This kit does not use the pre-filled cartomizers like the Blue or the nJoy kits, nor like the kits they carry at Wal-Mart (Fin and Mistic). The kit comes with battery charger. Two unregulated batteries (Unregulated batteries come off the charger at a higher voltage and the voltage drops slowly as the battery drains, where a regulated battery, like an eGo battery maintain the same voltage until it needs recharged), and two CE4 style clearomizers. It does not come with pre-filled cartridges. For these types of kits you actually need to buy the ejuice separately to fill the clearomizers.
The kit is $44.00 + the cost of e-juice + shipping, but you can get 5% off your purchase by using the code: 5% off (this code still worked about 3 weeks ago when I made my last purchase from them).
If you are looking to get in with a low cost and a solid kit, that one will work. Mine is still going strong after three months of use and my wife is entering her second month with hers.
The best prices I've seen on juice comes from
Mt Baker Vapor - Electronic Cigarettes, USA made E Juice, and Accessories I will say though, that I have no experience whatsoever with tobacco flavored juices. Neither my wife, nor I, had any desire to use tobacco flavors. Some juice vendors offer sample packs, or you can buy small (5ml) bottles to sample them.
There is a TON of delivery systems out there and the trick will be finding one he likes. I personally don't care for the CE4 style clearos. They run $4-$5 per and I've only been able to get 1 - 2 weeks out of one at most and that was doing all the maintenance I could. Right now I'm almost exclusively using Boge low resistance cartomizers (atomized cartridge). It has a polyfill on the inside that holds the juice. These things run about 1.50 or so each but, with a clearer e-juice I can get 2-4 weeks out of one. There is a slight learning curve with filling them though with juices with a higher VG ratio.
Which brings up another point. E-Juice is usually a mixture of Propylene Glycol (PG), Vegetable Glycerin (VG), Flavorings, and Nicotine suspended in either PG or VG. PG is thinner and provides some throat hit that smokers are accustomed to and carries flavor better. VG provides more vapor. Higher nicotine juices will also come with more throat hit. My wife and I smoked light cigarettes and 12mg juice was fine for both of us. Juices that are very high in VG are more difficult to get to soak into the polyfill in cartomizers (a lesson I learned the hard way) whereas 100% PG juices soak right in.
I've tried 3 of the brand of automatic e-cigs you buy in gas stations and big box stores (Blu, Mistic, Fin) and for me, all of them were inferior to the kGo Kit I bought. Ideally you may want to try to a vape shop near you and take your dad with you if you can. Usually you can sample juice flavors, etc, but always be wary of them trying to upsell you on things you may not need yet.
I smoked for 20 years and my wife for 41 years. We were both able to stop smoking completely the day our starter level e-cig kits arrived in the mail. Whatever you do, don't get overwhelmed. This is a great place for information from actual users of the equipment, and filled with very patient and very knowledgeable people.