28 Countries and Territories Rated... Based on being places visited in the past 3 years. 
I will update this list later as more places are visited. Remember this is just my opinion and based on my tastes and reflects the fact that I have visited some places more times than others (and may be bored). It is really hard to rate 25 places. Places listed as stopovers might be rated lower if they were listed as destinations in and of themselves so this also skews the ratings a bit.
 

2. Vienna  Lovely and grand city kept up well; great cafes.

3. USA   Good amount of things to see; reasonable prices and ease of tourism.

4. Canada  Quebec and Montreal are charming cities with decent shopping. A bit of Europe without the jet lag. Chilly winters.

5. Italy   Shopping for style; I like Italian food. Lots to see. If not shopping, would be much lower rated.

6. Spain  Much to see; pleasant place to be a tourist. Advanced infrastructure. But I like Italian food better.

7. Hong Kong  Shopping for custom made items. Nothing to see. Long trip to get there. I am to be there 3 days next month; I have no idea what to do there in between fittings.

7. Israel   Familiarity; emotional pull. Unrestricted eating (since I am kosher). Lots of friends. Aggravating though as a tourist.

8. UK.   Things to do; ease of tourism as it is English; had fill of London and theater has lately been disappointing.

9. France   Other places to see but exhausted Paris for now.

10.  Agentina  Good shopping, skiing, sightseeing and Buenos Aires is a lovely city. Much variety in the country's regions.

11.  Chile  Not as interesting in Argentina but also much variety in the country's regions.

12. Amsterdam  Saw it in winter which was a waste; should see it in summer. 

13. Dubai/UAE  An oasis of a stopover with nice resorts. Friends. Good shopping for Europeans. 

14. Cyprus  Good stopover with nice resorts; convenient location if I am in the region; friend.

15. Amman  Friends; pleasant stopover if I’m in the neighborhood.

16. Bermuda  Prettiest of the 4 stopovers listed above and more convenient from the US but overpriced. I understand that once Cyprus is reunited, the Turkish parts are pretty. So we will have to see later on what this means.

17. Greece  Not sure I care but I haven’t seen anything other than Athens and it continues to pleasantly surprise me.

18. Puerto Rico  Reachable tourist destination but not much to do.

19. Turkey  More to see besides Istanbul but not totally civilized. 

20. Germany  Seen most highlights except to Munich. More friends than in Belgium. There’s something about being in Germany I don’t like. Every time an ambulance comes around and I hear the sound of the siren, I feel they’re coming for me. Too much Hogans Heroes in my history.

21. Belgium  Pleasant place kept up well, better than Germany. Not much to do after several visits. Friends.

22. Kuwait  Nice place to go if you have friends but not much to do. 

23. Tokyo   Strange place and food is not to my taste. Not much to do there. But it is safe and I have friends there. 

24. Beirut   Will be nice in a few years. More free and lively than Syria but still a bit scary and bombed out.

25. Syria   Some good shopping. OK as a tourist with more than Damascus to see. For now, actually higher on the list then Lebanon but it is less free although maybe safer. Serious language problem.

26. Moscow  Scary and third world; bit of Pirates of the Caribbean feel; see it once; not tourist friendly. At least Syria feels safe and they are not ripping you off as a tourist.

27. Saudi Arabia.  Nothing to see really, and not a place you are welcome as a tourist. In fact, there are no tourist visas and it is a highly restrictive society. But at least it is very safe and in much better shape than Moscow. I personally would rather return to and be in Saudi than Moscow but this list is also meant to be relevant to you.