The apartment is in a hip/historical area and prices have gone wild over the past few years, especially if the unit is knocked out- like on the level we renovate our flips to.

It's wildly inappropriate - or at least highly unconventional - for the realtor to have asked for it.

I'm new to the Hanover area - since I'm very green perhaps we can help each other out - or at least share stories and thoughts in this wild REI world

It's really hard to make sweeping statements about neighborhood or property class, as these can vary wildly across town and even from street to street or block to block.

BUT, BUT, BUT, Section 8 will then get their grubby mitts in and they will decide how much rent you can charge. 

But there can be wild fluctuations from between places that are similar on paper. 

Not sure that I've ever heard of a market that exists where that math actually lives in the wild.

HOWEVER when I was 30 years old wild horses couldn't keep me from trying it.

You may be thinking purely of the property-finding aspect, but there's a lot more to consider.First off, as an unrepresented buyer, the only sellers who will take you seriously are usually going to be FSBO's, who may not know any better, or scumbags who know they can take wild advantage of you - any listing agent worth their salt is going to see an unrepresented buyer as a tremendous liability and amount of work for themselves and their seller. 

Each insurance company will have a different quote on what it costs to rebuild and the costs could be wildly different.