Personally, I'm a Self-Storage Guy, so I'd perform a basic feasibility study to see if Self Storage Would work in this market, and if not, then pursue a conversion to the larger units.  

In exchange for this permission, the Tenant agrees as follows:1.To keep no more than 1 domestic dog(s) as described below.2.To pay additional rent in the amount of $ 0 per month; or3.To deposit with the Landlord a "Non-refundable Pet Deposit" in the amount of $ 250 which shall be held as security for the faithful performance of this pet Agreement and shall be used upon the termination or expiration of this Agreement for the purposes of cleaning the Premises.4.To keep the pet from causing any annoyance or discomfort to others and to immediately remedy any complaints concerning the pet.5.To keep the pet from damaging any property belonging to the Landlord or others.6.To immediately pay for any injury, damage, loss, or expense caused by the pet (In this regard, it is expressly understood that at no time shall the Tenant apply any part of the Pet Deposit towards such amounts due, but rather, the Tenant shall make restitution immediately and separately from the Pet Deposit.7.To keep the pet under control at all times.8.To keep the pet restrained, but not tethered, when it is outside of the Premises.9.Not to leave the pet unattended for any unreasonable periods.10.To hold the Landlord harmless from all liability arising from the Tenant's ownership or keeping of the pet, including but not limited to any liability resulting from the Landlord turning said pet over to local pet policing authorities should the pet be found unsupervised.11.To dispose of the pet's droppings properly and quickly.Also, to coordinate the cleanup of the pet’s droppings with the weekly lawn maintenance.12.To insure that the pet will wear the appropriate Local Animal License, a valid Rabies Tag and tag bearing the owners name and phone number.All licenses and tags must be kept current.13.Tenant agrees to control flea infestation and will exterminate if necessary, and upon demand, in any and all areas affected with full cost to be paid by tenant. 14.Tenant agrees that Landlord will not be responsible for the injury, harm, or death of the animal, and agrees to hold Landlord harmless for any damages suffered as a result of any harm caused on the animal or by the animal upon another person, guest or employee.

I am considering this also but I read somewhere that the home (or, in my plans. triplex) you intend to buy with that loan must not need extensive repairs.

Get a feel for similar homes and how they perform and how you can edge them out and do a little better.

I don't need it because I have insurance and I don't do anything wrong-This is an extension of #4.

I'd also perform a move-out walk through and use the deposit for repairs if necessary.

I have extensive experience in MA and in FL. 

It does not seem to be extensive; maybe 15% of the property.  

I see sometimes where an older owner has had a maintenance person for decades and stays loyal to them even though they have slowed down a lot which has affected the performance of the property.

Since I don't have a bunch experience, I usually do extensive research and just let the numbers talk.