WHAT IS A COST SEGREGATION STUDY?

I would say that your QI should be competitively priced, but the lowest price is not always the best. 

It is your first year when you get the major tax savings windfall due to cost segregation and bonus depreciation.

With insurance rates going up, best to find areas with the lowest operating cost.

Namely, that if a tenant (in this case accompanied by a whole family) ends up stop paying rent and I would be on the hook for both covering the mortgage and dealing with open ended legal costs and time.

These platforms typically have billing policies where you pay a per unit fee per month to the software and you get regular updates and support each month.There are a number of low-cost platforms available that are able to offer you a lower price by passing along some of the costs to your tenants (payment processing fees, applications, tenant screening, etc).

Ignore the $1,250 per month because that's your cost of housing, if you didn't pay that on the home you'd have paid that in rent so that's a non factor. 

Determining the cost on something like this is only something you'll be able to find out by talking to the city.

To leverage the equity for financing my next deal, a second mortgage seems like a more cost-effective option.

I would need to consult tax consultant for this however I expect to reduce my effective costs by ~$1,495/month (based on a 32% tax bracket).2.