I am an engineer who works out of his basement everyday and rarely is on the phone.

I'm being required to pay another application fee and then $600 application fee to hopefully get this approved by the Board to allow me to continue running the STR that they approved 6+ months ago. 

These are by far the least amount passive so do your due diligence on understanding how to run a successful STR business and researching local laws on allowing STRs.2.

When running your numbers, if purchasing a home that isn't new construction and less than $1MM, I would estimate 1% - 1.2% of the purchase price as your annual insurance premium. 

I would run this by your realtor/property manager to get clarification.

At this level of scale, it is almost the same as running an extra unit.

You've probably heard of big Landlords losing property, but only because they were flagrantly violating Fair Housing, running a slum, or otherwise violating the law in an egregious manner.

We have always said we will run our business, as much as possible, as if it's 10x the size it currently is.

They'll run your credit and b.g, (I always get this upfront because it's best to know this right away so I always ask people what their credit is and if they have anything that will come up on b.g. report.While waiting for the Appraisal we'll get the title docs back, once the appraisal comes back and the as-is and ARV values are solidified the terms of the loan are also set. 

I was told by another investor that I will run into a seasoning problem, but i don't see how if i don't plan on refinancing.