If we are now losing $300 per month, that would be the equivalent of letting her stay there 6-10 more months, plus the turnover time of one more month in rent.

Your problem is that in the bank there is 0 chance of them losing any money and with you they could actually lose more than what they put in.If I put 10k in a bank I am certain that 2 years from now I can drive up and pull my 10k back out.If I give 10k to you you could spend my investment either doing a crappy remodel or not even finish the remodel and then walk away. 

She says they’re like cars and have a short life span and lose all value very quickly.

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?