On a scale of 1-10, with "1" indicating minimal repairs needed and "10" indicating a gut job, this house is likely a ~6-8.As such, we'll be doing a good chunk of renovations and, as a first step, we're currently in the process of getting a detailed as-built floor plan created by a local firm.We're looking for recommendations of good, investor-minded planners/designers to help us create and design our renovation plan. 

Get yourself a tax strategist - a CPA, an EA, a financial planner or a similar professional specializing in real estate.

For example, planner A wants $6000 for drawing and building permit application, and planner B wants only $1500, and even ask them to come on site would cost $500 each time.

Regardless you may want to talk to a CPA or financial planner to see what’s best for your situation.

I did already confirm with city planner I can build a duplex.

I'm assuming I can't just withdraw x amount from a business account to use personally (for money laundering reasons), and have been trying to research and come up with other solutions (hence why I'm speaking with a financial planner next week) and would love to know if anyone in this community has been in or dealt with a similar situation.

I'd run your plan by an accountant or a financial planner or at least a financially smart buddy.There're ways to postpone your tax, but it will lock up your cash that you plan to use for the mortgage payoff, so it may not work for you. 

If you do want to be a landlord then there are a few things you could do.First, do you have a financial advisor, wealth planner, estate attorney, etc?

My good friend used to be the city planner for the town that it’s in so I’m thinking he may have some valuable input or maybe know somebody who does.

Hi @Catherine Javier,Though you may not be qualified as Real Estate Professional, due to your W2 job, you may be able to meet the Material Participation rules if you manage your STR yourself.This will allow you to write off your losses against your W2's taxes (and if you do a cost segregation, these losses on paper could be very beneficial)Having said that, I am not a CPA and highly recommend you talk to your CPA and Tax Planner for more info.Good luck!