They typically want two years of work history before they will loan, so it's possible that you won't even qualify for a loan for quite some time.

That typically isn't allowed for a non RE pro (with exceptions/limitations).

Is this a typical scenario?

It appears some folks are confused about the way this coverage typically comes into play.  

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

Are these terms typical for cell tower leases or are they as bad as I think?

You pay a little more in interest, but the loans typically pay off quickly, and the interest is negligible. 

Being realistic, conversions to actual bookings are typically low.However, doing your research on potential travel influencers is key and understanding their packages & deliverables.

I think I would work towards positioning him to be successful in a typical job, build savings, and position him to be able to do a more traditional purchase.  

Trying to get a sense if it's even worth exploring this on a smaller scale like I'm talking about.You don’t have to do anything but professionals will typically yield the best results (and save you a lot of time filing or potentially refilling)