We were told the addition of any other pet-related up-front charges would likely not be considered favorably by a judge. 

In addition, the company that they recommend we work with, Prime, helped me set up my companies and though I repeatedly asked them if there were any differences in how it was set up because I was a Canadian, I was told that the way they suggested I do it was the right way.

Seller will be taking a 30k+ loss with this route.325k with 50K down to seller, 3 years of payments $1600/month, and a balloon payment of 215k at the end of 3 years.Benefits to me: (1) 10k less downpayment, (2) with the conventional route, the loan would be at 228k after 3 years of payments, so I will gain additional equity with the 2nd option since I will owe 215k (presumably I will have to refinance at that time).Benefit to seller: she gets over asking price, 50K upfront and $300/month of cash flow.Does this offer and structure sound reasonable?

There are a lot of market-specific issues you'll have to grapple with and also, there are plenty of landmines in MFR on its own in CT that you'll have to be ready for, in addition to the nuances and complexities of developing something like this.

Additionally, the boots on the ground partner has to be extremely trustworthy.

In our market it is important to make sure they are a licensed broker, carry adequate GL and worker's comp (and name you as additional insured).  

Additionally, we have developed templates for tracking key metrics that we require our PMs to fill out weekly. 

I could buy a LOT of umbrella (additional liability) insurance for $13,000.

Additionally, I'm working with the RE Ally Property management team, who was able to find a tenant to rent at slightly above market rates without any vacancy.

Prices a few years ago were based on expectations of (in addition to interest rates staying low): - Then current operating cost assumptions (like insurance cost expectations being flat)- A seeming disregard for record levels of new inventory / supply hitting the market- Extremely high inbound migration expectations which are likely to not be met, due to both natural disasters and the boomerang effect when people from California or the Northeast move to the American South and hate every minute of the humidity, the large and relentless swarm of insects, and the occasional hurricane.