I think mid-term rentals are a great strategy for a house hack, if you're in a good mid-term rental market.

I do think focusing in on one path and one goal will help me succeed.

We do want to get the appropriate permit but I am thinking that will take a lot more time and additional expenses to have it all in order and we need to be able to refinance it since we are purchasing cash (we are having a hard time with a lender which we initially wanted to do a rental 30 year loan, but not sure if there will denied due to this non permitted alterations to the house). 

Just think about the worst damage a tenant can cause, such being liable for setting your rental house on fire or burning down your rental house and the neighbor's house, etc.

I think you would have to force appreciation via property improvements to see any appreciation gains.

I can never know for sure if the pipes or wiring was replaced (my biggest concern), I don't think an inspector can actually tell as well since you have to tear down the entire house.

I don't think cap rate for residential RE is necessarily the best metric, but I try and achieve a 10% minimum gross rent to purchase price figure, so a $300K property I am hoping to achieve a $30K/month gross income goal.

Unfortunately, he made the common mistake of thinking he could borrow his way to wealth.

Malarkey 30-Year Dimensional Shingles.I have gotten estimates ranging from $5,500 - $7,500, which all seem like total rip-offs to me given the small size of the house.What do you think?

Think micro market within a market.