Demo expense can be $12k to $60k.Then hire an architect and get permits.

An electrician rarely hires another electrician for example. 

Work property mgmt numbers into your analysis just to make sure it still cash flows if you want to hire it out one day.

The issue is I just made my first high salaried hire and that in itself is somewhat of a risk for us.

It is possible but you need to be aware of few things:You can't manage it yourself, meaning you would have to hire a property management company.

A tenant can simply have the local family doctor or counselor sign a paper who knows virtually nothing about dogs or what an esa is supposed to legally provide as a service .

Simply put - hire a Property Manager as the Realtor to help you find and purchase the property. 

You can make a lot of money on Contracts For Deed, but I generally find the whole process to be ethically / morally questionable for me.I realize there are different Sellers and all situations are different, but a lot of what I see are Sellers who take a large down payment from someone who they know has virtually no chance of ever paying off the property.They wind taking the property back the first time someone misses a payment and then they start the process all over again.

I do not hire out this work, for two reasons. 

When an employer in hiring mode gets flooded with resumes, somehow they have to eliminate candidates, and they do consider experience.