I would put in the inspection objection that the roof is to be inspected and make sure that it is up to code before closing on the property. 

@Caleb Bryant"Zoom meeting for like minded real estate investors to collaborate, share insights, suggestions, resources, ask questions, and grow.The object of the meeting:To educate ourselves more about the real estate market in the areaTo share resources for greater success and efficiency in growing our portfoliosTo create synergy by working together and making connectionsThe call is open to current investors, beginning investors, and those thinking about investing in the area.Please come with questions for the group or experiences to share."

I tried working with them on a solution to meet both of our objectives, but they wouldn't budge on prohibiting property owners from visiting their own property without prior approval from the property manager. 

I would waive inspections if i knew i were purchasing a real "cash cow" because if the deal is objectively good enough fixing the mechanicals might still be worth it.

Well, most towns do not want multiple detached dwelling structures on one lot, so finding an empty lot with zoning that permits multifamily, with no town objection to detached dwellings will be kind of like finding a unicorn. 

The ultimate objective is to sell one of the houses and utilize the second one for Airbnb purposes.While I have prior experience with Short-Term Rentals (STR) and Long-Term Rentals (LTR) properties, venturing into construction from the ground up is entirely new to me.

That's not the object. 

Fact you do make higher returns out of NYC if it fits someone's objective it works but it ain't NY baby!

Another shinny object will present itself.I'm glad I'm went through this. i'm learning what to look out for as i gain experience.

An important question for your strategy has to be- what are your objectives?