LL won’t return security deposit!!

By Beans331

I am a CT renter who has a problem getting my former landlord to return security deposit after moving out. This is not the first problem we have had with this landlord. First of all, upon moving in to the house the LL wanted 3 months security deposit bc he was wary of my SO’s credit- for the two years that we lived there rent was always paid on time. We negotiated that we would pay only two months security $2100 but would clean, paint, and install carpet in the home. The house was a disaster and we spent the month before moving in cleaning and making improvements. He also wanted us to fix basement windows which we never completed bc found it was too big an ordeal. I am now aware that in CT the maximum security deposit allowable by law is two months rent which we paid.
Shorty after moving in there was a major snow storm which caused the shed and roof to collapse, causing damage to our child’s bedroom and making it unlivable. For 3 months he was without a room and we paid full rent. An insurance appraiser came to the house and appraised the damage for the LL and presumably cut him a check. The bedroom was finally fixed but the shed remained in the backyard and he just put a tarp over the roof. We hounded him for a year about fixing the roof- he claimed the insurance company didn’t provide enough money to fix it. I assume he spent the money. Finally after a year, he showed up in November with friends to fix the roof himself. Much of the house was "fixed" by him, including plumbing and electrical work that he clearly had no clue about. 
We initially signed a year lease and when that expired we never signed a new lease. We lived there another year, sent him a certified letter of our intent to move and forwarding address. Before moving we repaired any damages and cleaned extensively and took photos and video to document the condition we left it in. It was in much better condition than when we moved in. On the 30th day after we moved, we received a certified letter from LL stating that due to the holidays and waiting on estimates he will need more time to assess damages. First of all, there were no damages. Secondly, even if there were, doesn’t he have to abide by the 30 day deadline or does his letter buy him more time? He also never paid interest on our deposit. We asked for the account number of where our money should be in escrow with no reply. I believe he spent the money. We plan to take him to small claims for twice the amount, but would like opinions/ advice from others. Also, could we get reimbursed for rent paid while damaged or the work we did upon moving in??

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