Here’s a list of items to check as for the date and perspective of a map you come across.
Bold items are very macroscopic points, and probably noticeable first.
Italicized items are very microscopic differences, and might not be distinguishable on global scales.
Note: these lists are nowhere near exclusive, just a sampling of items to check.
A) Is it outdated?
0) Is South Sudan part of Sudan?
1) Does it have the Soviet Union?
2) Does it have Yugoslavia? And is it the big Yugoslavia or the small one?
3) Does it have Czechoslovakia?
4) Are West Germany and East Germany split?
5) Are North Yemen and South Yemen split?
6) Are North Vietnam and South Vietnam split?
7) Is Bangladesh called East Pakistan?
8) Is East Timor part of Indonesia?
9) Is Montenegro part of Serbia?
10) Is Namibia part of South Africa?
11) Is Papua New Guinea part of Australia?
12) Is Egypt the United Arab Republic?
13) Is Syria the United Arab Republic?
14) Is the United Arab Emirates the Trucial Coast?
15) Is there a Zaire?
16) Do the Cooch-Behar enclaves exist?
17) Is Kiribati united?
18) Is Hong Kong part of the United Kingdom?
19) Is Macau part of Portugal?
20) Is Tanzania united?
B) Whose perspective is it from?
0) Is there a People’s Republic of China (“China”), a Republic of China (“Taiwan”), or both?
0a) Is Tibet part of a China?
0b) Is Mongolia part of a China?
0c) Which China is Kinmen in?
0d) Which China is Lienchiang in?
1a) Is Hong Kong part of a China?
1b) Is Macau part of a China?
2) Is there a Republic of Korea, a Democratic People’s Republic of Korea, or both?
3a) Is Jammu and Kashmir part of India or Pakistan?
3b) Is Azad Kashmir part of Pakistan or India?
3c) Is Gilgit-Baltistan part of Pakistan or India?
3d) Is the Shaksgam part of Pakistan, a China, or India?
3e) Is Aksai Chin part of a China or India?
3f) Is Arunachal Pradesh part of India or a China?
4) Is there an Israel, a Palestine, or both?
4a) Where’s the boundaries between Israel and Palestine?
5) Is Golan Heights part of Syria or Israel?
6a) Is Crimea part of Russia or Ukraine?
6b) Is Donetsk part of Ukraine or Russia?
6c) Is Luhansk part of Ukraine or Russia?
7) Is Kosovo part of Serbia?
8) Is Abkhazia part of Georgia?
9) Is South Ossetia part of Georgia?
10) Is Nagorno-Karabakh part of Azerbaijan?
11) Is Transnistria part of Moldova?
12) Does Armenia exist?
13) Is there one Cyprus or two?
13a) Is the entire island of Cyprus part of a Cyprus?
14) Is the Hala’ib Triangle part of Egypt or Sudan?
15) Is Abyei part of Sudan or South Sudan?
16) Is Somaliland part of Somalia?
17) Is Socotra part of Somalia or Yemen?
18) Is all, some, or none of Quebec part of Canada?
19) Is French Guiana part of France?
20) How are claims in Antarctica distributed?
21) Is Mayotte part of France or Comoros?
22) Is Abu Musa part of Iran or the United Arab Emirates?
23) Is Ambalat part of Malaysia or Indonesia?
24) Are the Paracel Islands part of a China or Vietnam?
25) Are the Spratly Islands part of a China, Vietnam, the Philippines, Malaysia, or Brunei?
26) Is Dokdo part of a Korea or Japan?
27) Is Diaoyu part of a China or Japan?
28) Are the South Kuril Islands part of Russia or Japan?
29) Is Olivenza part of Spain or Portugal?
30) Is Šarengrad part of Croatia or Serbia?
31) How is Macedonia recognized?
32) Is Navassa Island part of Haiti or the United States?
33) Is Serranilla Bank part of Colombia, Nicaragua, Honduras, or the United States?
34) Is Bajo Nuevo part of the Colombia, Nicaragua, Jamaica, or the United States?
35) Is Earth a colony of a foreign galactic power?