Whether the man will let her practice the religion or not is irrelevant and such marriage isn't permitted under Islamic law unless he would become Muslim.
If all other shar'i requirements are met, yes, she can marry that man.
The marriage proposal must take its normal procedure, primarily around the parents giving their consent and their blessings. This is the most important part.
A second important step is to see the character traits of the person, their moral standards, their family, compatibility, etc.
A third step to take is seeking consultation and advice, trying to find out if this prospect marriage is a good idea, and the obstacles they might face. This is necessary for any case of marriage, Muslim born, or convert.
Both of them should study this from all its angles, for the sake of making the right decision and having a successful marriage.
Your late wife must have been a good lady for you to continue to remember her. Yes, of course you can do dua and pray for her forgiveness, as long as she was not hostile to Islam and she knew no better.
Islam preaches inner and outer modesty, and as human beings, we feel more safe and secure when we are covered up. This is why all religions somehow promote covering up and not being exposed for onlookers to see.
If a non-Muslim wishes to dress modestly, then of course that will benefit her. If she wishes to dress like a nun, or as Muslims, then that is also her choice, and it would not be considered as being 'inappropriate'.
In the case of a Muslim woman, or non-Muslim, wanting to, for example, enter into a holy shrine, there is a requirement that she does wear an abayah/chador. It is not Islamically mandated, but just out of respect.
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