It's too risky for me to do it.
I think it depends on the country you live in.
Restrictions are more severe than in developed countries, and Microsoft A1 has come to crush quite a bit, so I don't think I will do this business.

I'm only using the Open Licensing contract for personal use.

How likely is it to get caught and banned? $700 is quite a sum, One would at least need to sell quite a fair bit of keys to breakeven, I would assume it is not common to get caught and banned since forums like this and aihao.cc members frequently post keys out to the public, If Microsoft tracks all those keys, Thousands of MSDN accounts would have been banned by now easily. Please correct me if im wrong. Thank you.

Must be contracted from a Microsoft representative in your country.

https://o365hq.com/license/77d-00041

You can get it by subscribing with MSDN like this.
However, if you sell MSDN keys, you may be banned.

I appreciate your swift response, Are there any other  verification criteria for MSDN application apart from the $700? I mean one would get way more out of the license by reselling the MSDN key like they are already doing $700 per year is nothing tbh. Say if I would like to get it is it a publicly available program to join? If so, how?

The Microsoft A1 administrator account is a school administrator, and since I am a school corporation, I apply to Microsoft to let me use it for free with an educational institution discount. If you get an OK from Microsoft, you can maintain it for free unless you get banned from Microsoft.
An MSDN account costs $700 per year. You can't keep it if you don't pay for the year.
However, you can generate any number of free keys few per day.
That's a key of type OfficeXX_ProPlusXXXXMSSDNR_Retail.
By selling these they keep MSDN subscriptions at a profit.
So MSDN subscription accounts are never sold.