It should be your primary concern in doing the numbers. 

I would be very concerned if you engage him to be your professional!

Assess the convenience of any potential investment property by considering typical walks to class, libraries, or—if applicable to your town—a downtown area (think shops, restaurants, or bars).Don’t expect tenants to sign long-term leases.Considering that the majority of renters will be students, tenant turnover will be high—undergraduates especially tend to change housing year to year, meaning renters who are willing to sign a lease over one year will be few and far-between.Instead, encourage lease “pass-downs”.One main concern in real estate investing is vacancies—a valid concern, especially in a college town, where the rental off-season between semesters will deplete the prospective rental pool.

Assuming you sign a year lease with the tenant, both of these concerns can be set to rest with the lease.

My concern is protecting my investment, not his budget.

I am concerned the cost of remodeling may be expensive because the existing ceiling height is only 6.5 feet so we would need to lower the floor by at least a foot.

With that said, keep an eye on your credit, of course, yet I wouldn't be overly concerned. 

Clearly they are built to 175 mph wind standards today, so that shouldn’t be a concern.  

Because from what I see  listing, I have concerns about not finding something cash flow positive-what do you expect long term from the York area in general (not real estate valuations necessarily, but do you see the area changing any particular way over the next few decades)?

I also think the rent amount is too high for a venmo transaction but I have the same concern for using venmo as I do for Paypal.