If the Loan-to-ARV ratio will stay below 65-70%, some HMLs will allow the interest to accrue and be paid at the end (and the points as well), though likely these accommodations will necessitate the borrower having a proven track record for flips.

Once I familiarize myself with my states RE laws and licensing I would highly consider this tactic as it would be a starting point that accommodates my low budget situation.

I have an RM2 property and the planning dept stated that my lot size would not accommodate a third unit. 

They certainly are not going to add your property to their list of available housing for students, but all gave me suggestions on how to advertise vacancies to inbound students, and note that many students (think professional studies) are adults with families, who are seeking accommodations that are family-friendly (one housing rep flat out told me that they run out of family accommodations months in advance and always get asked about help finding housing around the schools)...Food for thought.  

Until they make a formal request for reasonable accommodation, you are under no obligation to do anything.

How do you accommodate for sq ft pricing and product price tiers?  

Murphy exemption" (web search it).Your best bet is to consult a local attorney whom can advise you of your options ("reasonable accommodation" if another tenant in the building is highly allergic, lying on application to disqualify, etc.)Unfortunately, most ESA letters are scams, which marginalizes the legitimate folks.

That will apply to the roof required to be repaired/replaced to accommodate the system.Fannie Mae allows for a full appraisal of the value of the system in appraising the property IF the system is owned/financed.

I spent about $15/sqft setting up a Galveston TX STR recently and imo it has better accommodations and decor than 90% of comps in my market.

In the current municipal market, I don't think that we can use the land to accommodate more trailers.