H&C grounds comes into effective in following cases when applying 1) for travel document (outside Canada) 2) for PR card renewal and also at POE if one is subjected to immigration assessment (inside canada). Do you agree?
I agree
Therefore, why would someone take chances trying to sneak into Canada without meeting residency obligations when can be reported for not meeting residency obligations by immigration officers at airport and might get removal order?
Some people don't have any H&C grounds for not meeting their requirements or very shaky ones in which case they may like their chances better if they simply enter Canada with their still valid PR card, take a lecture from an immigration officer or not, enter Canada in most cases without being reported, wait for 2 years until they meet the requirements again and then apply to renew.
Perhaps it is better solution to apply for a travel document on the same H&C grounds before coming to Canada.
1) I might be mistaken, but isn't better to apply for travel document on H&C grounds at the first place?
You can not apply for a travel document if your PR card is still valid. If your PR card is still valid, you are expected to go to Canada and present your case to the IO or just enter without presenting your case if nobody asks as you will have to deal with it anyway at PR renewal (unless you wait for 2 years).
2) What are your thoughts on the following ..... If Canada could have a benefit from an applicant (e.g. who has job offer, educated in Canada at graduate level) seeking to renew his PR status as was away more than 3 years out of Canada, there might be good chances for one to get a positive response from CIC and permitted to get into Canada without problems.
I do not think that they would look at your credentials to decide if you get to keep your PR or not. You already presented your credentials when you applied for PR. You got your chance but you decided not to stay.
By the way, here is the immigration manual for PR Status determination:
http://www.cic.gc.ca/english/resources/manuals/op/op10-eng.pdf