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One option that may help in such a situation is to have a negotiated, temporary period of time where the rental agreement is month-to-month, a.k.a. "tenant at will." This trial period might be preferable for a scenario in which a tenant is looking to gain the trust of the landlord.
In cases such as this, an off-season rental (ie: not beginning on September 1st) could add to the arrangement's appeal to both parties. If for any reason, the renter pays late, the landlord can terminate the arrangement ASAP, and for the renter, if they want to find a more eager landlord, they'll be looking to start renting in a month when most people are not.
Keep in mind that Cambridge is a highly sought after city for rental properties, so all year round, it may be difficult to find an ideal situation. Somerville is not too much farther and may have more options.