I had to pay $600 to have the roof fixed, so since it wasn’t fixed and I have signed statement from the roofer that there is no evidence of repairs ever being made, can I take him to small claims court?

Are you going to go to Craigslist and find the first person who claims they can do it and go with them?

I noticed a few threads on here complaining about reasonable claims getting denied by the insurance companies they work with.

What I have found out since posting is that owners are unrealistic on what they can get out of the property and are not willing to drop down that much. 

I also went down the 203(k) rabbit hole last night and from what I can tell, they will allow you to claim 75% of anticipated rental income but that information was just from a Google search. 400 to 500k does not get you much around here unfortunately.  

Plenty of ways to get a good desired solution.I do not like Postcardmania because they CLAIM to be all you ever need in the world of postcards.

If there was no security deposit retained at the start of the lease, you could probably pursue this in small claims court. 

@Kevin Drouillard most PMCs do not pursue collections after a tenant moves out.Check the eviction judgment to see if a money judgment was included.If not, you will need to pursue small claims judgment.Once you have a money judgment you can try to garnish (another court process) wages, bank accounts or state tax refunds.

What are you doing so grossly negligent that your insurance company would not cover an insurance claim on ?

He said he is willing to get creative with the structure.Asking Price is $1.5M, current gross income is $80k which he claims he could "easily" get it to $100k, but he likes sticking with his long term tenants.