Q: When it comes to marriage and finding a spouse for sisters, things aren't always fair, halal, or easy. How are we supposed to know if "someone’s deen is good?"
A: What you have stated is indeed true when it comes to judging a person's deen. We can only judge a person from what he/she makes apparent in front of people and not what is in the heart as that is solely between him/her and Allah SWT. By just a mere 'Yeah, he prays.' is not good of a justification that the brother's Deen is good as a person's Deen is not focused only on solat but other things too.
A person might seem to be a practicing Muslim as far as the eye can see but who knows, he can be a munaafiq (hypocrite) at the same time. In another case, a person may seem to be indulging with sins but from the bottom of the heart, he has been trying and striving to become a true mu'min (believer) but, unfortunately, falters every now and then.
Similarly, when it comes to choosing the right candidate. Rasulullah SAW has advised us to look at a person's Deen as compared to wealth, beauty and lineage. When a person's Deen is good, insya Allah his dealings with others, characteristics, composure will be in accordance to Islam and Syari'ah as the other things mentioned (wealth, beauty and lineage) are temporary things.
One way on determining whether a person's Deen is considered to be good or not is by looking at the person's family. How are the person's family members when it comes to matters of deen? Do they give preference to what Allah SWT and His Prophet SAW say? Do they establish their daily prayers punctually? What about their fasts in Ramadhaan? Are their zakaah paid on time? Are they observing the proper Hijab and niqab?
When we are aware that the entire family practices in accordance to Syari'ah and Sunnah of Rasulullah SAW, then automatically and naturally our mind and impression towards each and every member of the family would be, "They are practicing Muslims and their Deen is good." Although, not forgetting, there can be cases that the entire family is not practicing but only one or two are and vice versa. However, to see whether a particular individual's Deen is good or not, will have to be decided separately.
Another way to establish whether a person's Deen is good or not is by observing one's company. We can usually get an impression on one's behavior and characteristics by looking at one's company as the saying goes, "Birds of a feather flock together." which means that people with the same interest will group together. So, if a person's group of friend is punctual on solat, obedient to the parents, avoids Haram communication with na mahram, likes to engage in dhikr, recites the Quraan frequently etc. then we can safely conclude that insya Allah, that individual's Deen is good.
On the other hand, if a person's company is of those people who are very negligent in solat, vulgar in speech, disrespectful to elders and parents, enjoys going out to Haram places, likes to waste time etc. then immediately we would say that that individual is not a good person and his Deen is not good either.
When a person receives a proposal, matters that are doubtful or unconvincing, should be investigated either during the time the male and female speak to each other (with a mahram present) or even by inquiring from the mahram of the candidate - the sister can ask the brother's mother or female relatives regarding the brother while the brother can also do the same when asking about the sister via her father or male relatives.
Then, after the meeting, the sister and brother can then sit and discuss with their family for opinions and suggestions. Istikharah would be the subsequent step as to seek guidance from Allah whether to proceed or not with marriage. If for some divine wisdom of Allah SWT, both of them were not meant to be, then so be it. Allah SWT at the end of the day, has something better in stored for the both of them and they should have full yaqeen (conviction) in Allah's decision.
It should be noted that there is nothing wrong in desiring and wanting a husband/wife with certain qualities which sometimes may seem far fetched. We should always remember that Allah SWT's treasure is vast, therefore, ask from Allah and nothing from Allah's treasure will decrease in the least. Insya Allah, Allah will grant us the candidate that fits our criteria and at the same time suitable and compatible with us.
One thing to be reminded is that, it is good to have certain expectations of things and people but everything besides Allah SWT has a flaw and only Allah SWT is free from flaw. Thus, it would not be wise to be too picky and choosy. When a good proposal comes knocking at our door, don't let it go just because 10% of the criteria could not be met as we may never know when someone with a 90% criteria will come again.