I think you're a guarded and careful person, but residential rental real estate is a kind of dirty business.

Without the upside of a good neighborhood and/or quality property, I don't love it. 

An owner of a higher listed property may be willing to take a steeper discount than a lower priced property where the owner is stuck at their list price.

If the current wood ones are ok leave them.

Really sounds like more of a publicity stunt than anything else. 

We just offered on a house with all contingencies waived and after the depositing the initial deposit we realize they are counting 300 sqft of completely unfinished room with no ceiling hvac huge  unit in it and with all sorts of pipes taking floor space and ceiling space as a room of 300 sq ft.This is misrepresentation as it makes the house so much smaller in the basement and we are already paying above asking by 50K.

I'm a real estate investor in other parts of the country but not NY due to the extremely high buy in price.

Is Reading, PA a Scalable Rental Market?

I've also been thinking of using a HELOC to acquire our next investment property, likely as owner occupied.

I'd get a quote from Steadily as mentioned, but Thimble is another one I read about in an AirDNA article.