7 or 14 day JR Pass

Hi - Female traveling with 2 indecisive men for 14 days. :)
Here's our itinerary:
Wed, Day 1 - Heneda Airport to Tokyo
Sun, Day 5 - Tokyo to Kyoto
Thur, Day 9 - Kyoto to Osaka
Sun, Day 12 - Osaka to Yokohama
Tues, Day 14 - Yokahama to Narita Airport

Is the 14-day JR Pass worth it or should we get the 7-day and pay out of pocket for the rest? They think it's more convenient to buy the 14 day so we don't have to worry about buying tickets at the train stations.
What do you guys think?

Regular tickets will come considerably cheaper than a 14-day pass unless you plan some additional major side trips that are not listed on your schedule.

As for a 7-day pass, it won't pay off, because the only two long-distance trips cannot be covered by a single pass.

I agree with Uji. Your timing in each location makes single tickets much cheaper as the Tokyo-Kyoto-Osaka-Yokohama covers eight days. Even if it was only seven days the 7-day pas would not save you much (if any).
Tokyo to Kyoto 13,080 (non-reserved)
Kyoto to Osaka Y590
Osaka to Yokohama is only Y13,290 (non-reserved)
Total less than Y27,000 where the 7-day pass is Y29,110

And, yes, you can get reserved seats with the JRP, but it's not really necessary if you are trying to save a few yen. And while the 7-day pass might be useful around Kyoto/Osaka, you still have to mess around doing the voucher exchange and a bit more travel to get any decent savings.

Neither. 7 day pass wont pay off also.

They think it's more convenient to buy the 14 day so we don't have to worry about buying tickets at the train stations.

Just picking up on this comment in the OP, to get reserved seats you still need a ticket. If they are happy to go non-reserved, then, yes, you can avoid that, but you still need to do the voucher exchange.

And, the pass will be more expensive.

Suggest to them that you will do all the tickets for the trip and they pay you the Y46,390 for the 14 day pass. For the two of them you'll pocket a over Y30,000 and your travel will be free in exchange for a little bit of time buying their tickets, but you would be getting yours anyway. See what they say to that :)