It took way longer than I planned and too many things went wrong like the well failing after winter.

It's based on past experience of having tenants fail to have a successful lease.Yes, today you are making your $975/month rent payment with no problem, and my assumption is your month income is below $2,925/month since that would be 3x the rent, and your post is all about not making 3x the rent.So life if going fine today, but tomorrow your transmission may fall out of your car and need $2000 worth of work. 

I've filed for eviction on the basis of her failing to pay rent.  

If all else fails and they do get out your best bet is a collection agency or write it off and if they have a deposit you can keep that to cover some of the cost.

I would not play with fire when it comes to failing to disclose.   

@Jeremy Willis - most of the salespeople / “coaches” at a recent one I went to either weren’t landlords or had failed, been foreclosed/bankrupted in the past.

Anyone do this before and fail?

The pump was on it's last legs anyways so it wasn't a huge deal as I was planning on replacing it but it did make a mess downstairs when it failed.

I got a letter from a pro bono attorney they contacted stating that they want to avoid court and can stay in the unit for up to 60 more days because we failed to give the written notice– is this true?

You can offer ~ $200 DDFee.You can offer to SHORTEN the DD Period( if the water/power utilities are on , see how fast your home inspector can get there for a verbal pass/fail to you ) To be followed by the written report --BE THERE ON SITE DURING THE INSPECTIONS.Really you have to see what the seller will accept.