Your clients will have a separate auto policy and if you only write the home there's a real good chance you will lose the account within the next 5 years as they will want to bundle the two together to receive discounts.   

Almost no one  is much of a repeat  in my area,  so I feel no obligation to  let them cancel  so I can lose money.

I think you need to talk to the tenant and let then know that if you go to court and you win (which I believe that you will if they haven't paid like your PM says) then they will kick them off of section 8 and they will lose it.

I would say my risk tolerance is mid to high considering I am only 26, not saying I want to lose anything, but also just wanting to learn and refine the skill more than anything.

Value add deals are complicated; there are a lot of moving parts and each one has the potential to turn a deal south and lose you money.

I recommend setting up keyword alerts for each area as they are discussed in the forums daily with advertisements posted in the BiggerPockets marketplace hourly.One thing to note when looking at the individual markets, you can make or lose money in any market.

Did I lose track of your properties?

I did that twice and in 2008 I find myself wanting to Sell with the Market collapsing as all my renters lose their JOB's.

They will not be able to complete the renovation and have offered to let me take it over so they don't lose the potential profit from the property. 

Weird story: I am in a Facebook group and talked connected with a lady who is losing her home in Wood County, Ohio.