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Below are my thoughts to your questions-Seeking funding (brokers or creative) most likely FHAI'm sure there are many creative ways to get funding, but if you have a full time W2 job, FHA or conventional loan is probably the easiest way to go. 

- Should I expect to have an equivalent deduction from the full price that I pay for the home, or is that too hopeful? 

PMs make their money is every time they have to find you a different tenant then they collect either half - a full months rent.

While working full-time jobs we were able to demolish the dilapidated house, a garage, several sheds, and clear and clean our 1.3-acre parcel.

But it worked, and we got damn near full asking with multiple offers. 

I have briefly talked to an accountant and he told me that I’d need to pay the full portion of the capital gain tax In the US (as an individual property owner) and a less portion in Canada.

Her husband will not be living with her full time as he will be primarily living out of state, just visiting often, but I told her that he had to be on the lease.

Ok maybe.You will still have to pay to demo the damaged property and that can run from $15k to $40k or more depending on where you live so you may not have much left of your initial investment to buy that next property.And if you financed it - the bank is going to take the majority of the insurance settlement to settle the loan and you will own free and clear a fire damaged house that the city will eventually start making demands for you to repair or demolish.This is why the majority of lenders require you to carry full replacement cost coverage.

Most of the repairs are cosmetic, but in my opinion the home is in need of a full gut job.