Can I take legal action against tenant for breaking lease?

[Peter Chan]

I had purchased a 2-unit property in Florida purely based on location appreciation potential rather than returns back in early 2018.

The sellers as behind on his mortgage and needed to sell before he was foreclosed upon.  He lived in one unit and his relatives lived in the other unit. 

His realtor claimed his relatives were paying rent - but being the inexperienced fool that I was at the time I never asked for proof of deposits or leases. 

The seller wanted to stay and signed a lease for $2,000/month for one year.

At closing time I had retained a $10,000 deposit of his. I believed it was to be returned at the end of the lease and actually thought my lawyer held that money at the time but I’ll get into that in a bit.

Anyways - we close and the first month goes by and he pays rent. No issues.

The second month is where problems begin. He does not pay and is not responsive to the management company I hired.

Eventually he tells them that I owe him 10,000. After hearing this I asked my lawyer who did confirm he released the $10,000 to me. I immediately had a check sent out to the tenant for $10,000.

Another month goes by and the tenant does not pay - so now he is $4,000 behind on rent.

Also I know he has the money because even after his mortgage fees were taken out of the sale he still had hundreds of thousands of dollars in profit made from the sale.

The property was in very poor condition but he was living in it before the sale and accepted its condition enough to sign a lease. 

I had attempted to have contractors make repairs to his relatives unit and they never provided them entry. The contractors said they could hear noise inside but did not open the door on multiple days. 

Management did post an eviction notice to him.

About 3 months into this nightmare I was told by management that the guy and his relatives had left the property and it was vacant. They trashed it on the way out - literally throwing garbage all over the outdoor area and I received a violation from the city and had to spend about $1K to get it cleaned up.

I eventually sold the property at a loss about 5-6 months after purchasing it - around mid 2018. 

I have all the emails between myself and management still saved. Though my management company was absolute trash and constantly tried to scam me by overcharging for basic duties that other companies provide for free or at a reasonable rate. Management would get 10% of rent and claimed that even if the tenant did not pay I would have to give them 10% of the monthly rent contract each month. The contract I signed however did not state anything of that nature.

In the end I never did pay them (and they never asked me in spite telling me they would once) - even when I told them I no longer need their services they never asked for payment and we just stopped communicating.

I know this is long winded but can I sue at this point and is it even worth it?

The reason I had to wait between mid 2018 and now is because I was out if the country from then until the very end of 2019 dealing with family issues. Additionally I was afraid of the tenant’s relatives because he was from a place known for gang violence and one of his relatives living in the other seemed to fit that mold. At this point though I want to sue if it’s possible.

At the time of purchase I had an LLC for this property which has since been closed if that matters.

Edit: in case a new investor reads this and freaks out I have since purchased other investment properties and they have all been running well. Don’t let this turn you off. I was extremely naiive at the time.