You can't just say a dog is a service dog.

I would say as long as your debt/income ratio would still allow for a mortgage, keep the cash and the loan and use it to put down on a house.

As we get closer to the end of the month, say a week out or so, we will start showing up way more often, maybe casing the place for hours on end everyday instead of stopping by once every other day.

At that it would probably be them saying they need to get formal custody...If they are offering to null the lease and sign a new one adding the minor as a resident and offered to pay a little more I'd say a-okay to them on that.  

If you are taking the cash out long term, I would say a cash out refinance over a HELOC.

But I've always managed to find insurers.You can cover it with vinyl, but if you have a property with nice bones (say a nice, or even a middle class old Victorian) putting vinyl over it may throw off proportions of any attractive molding the building may have.If it's a property on Munjoy Hill/West End of Portland, you may want to consider remediation, as it would likely pay off in increased value/aesthetics/resale.  

I will say a lot of these comments are absolutely ridiculous.

I'm sure in WI they don't have any problem charging tenants full price for brand new carpets, no matter how old they are, as long as there is damage.And you never quoted any WI rules that say a landlord can charge full price for a carpet replacement, regardless of how old it is.Nope, you can't just give a link to the landlord tenant book.  

With this you can purchase, Let's say, a duplex or triple etc.

Let's say, as-is, it could have been rented for at least $400 more per month?