I will do Option #2. Getting from ITM to Kyoto will make Option #1 not any better than Option #2. The last train out of NRT Terminal 2 which will get you to Kyoto in same day is:

Narita Express No. 50
Airport Terminal 2: 7:52 p.m.
Shinagawa: 9:00 p.m.

Nozomi No. 263
Shinagawa: 9:19 p.m.
Kyoto: 11:22 p.m.

There are earlier trains than that, but above is the last train of the day to Kyoto. The more likely option for you will be:

Narita Express No. 44
Airport Terminal 2: 6:19 p.m.
Shinagawa: 7:28 p.m.

Nozomi No. 87
Shinagawa: 7:46 p.m.
Kyoto: 9:51 p.m.

or

Narita Express No. 46
Airport Terminal 2: 6:52 p.m.
Shinagawa: 8:00 p.m.

Nozomi No. 259
Shinagawa: 8:17 p.m.
Kyoto: 10:21 p.m.

P.S.
If you are going to do Option #1, from ITM to JR Kyoto station is an hour to an hour and a half journey depending on traffic. The bus from ITM to JR Kyoto station is 1,340 yen and a taxi will be about 20,000 yen plus toll.