With that said, there are many areas that will feel a DEEP depression like Detroit in 2010.

Yes, if I were in your shoes I would cover the cost of the girlfriend's background document, while having the boyfriend pay his own way.You'll want this info not just to ensure you don't have a problem now, but also to provide you with the deep personal data that might come in handy if you ever have to engage in collections activity against either of them.As an aside, when you purchase a rental property with tenants already in place, you should always demand all the tenant application and approval documents as part of your overall estoppel process.Once you buy the property, they become your tenants, warts and all, so you should know what you're getting into well in advance.

I tried to share every single red flag, concerns I had, pending issues, etc. with the buyer from the building, tenants, city, neighborhood, vendors, etc. but it is tough to get that support from all sellers. 

Though this is my 2nd deal, this represents a red flag (unknown as to what is in there and it's condition, the home is 110 years old) to me and among other smaller issues related to water stains in the unfinished basement (satisfactory) non working sump pump (can be replaced), water heater leaking (agent said will be replaced) , etc .. how should I approach this???

Only a local would know that homes on the east side of Route 3A are valued very differently than those on the west side, even though homes may only be a couple of hundred yards apart.The main problem is that you have to drill down deep to find this accuracy rating. 

The HOA is probably digging deep into the issue as well.

IF the properties and entire process is handled a certain way then some investors may get by and profit but you'll have to dig deep and determine if it's really worth it at the end of the day? 

Dive deep into relationship building. 

What red flags do you see?

Most of the people I saw said that it is better to continue the pitched roof with smaller pitch (see in red).