@Lucas Schlund the same thing that happened to all the STRs in NY City when their ordinance went into effect, as well as many other cities.Owners must comply and the government doesn't care about your potential losses:(

If I do this, will IRS (or any other government entity) start looking at me and wondering what's going on?

Okay BPers - I'm back yet again to pester you with obvious questions, but not so obvious to me since I've called the entire Baltimore City Government and no one seems to know how to use a phone (Called at least 10 numbers - maybe it's a snowday?).

I know there have been delays and issues during government shutdowns but this is a new one for me. 

Aaron - thanks for the post ...wedge area off Monroe is solid .....make sure your financing is in place and lined up  before  beginning to property shop ....traditional lender have  programs that allow as little as 15% down if the  rental propety is a  1 unit 

I'm looking to get their "package" which includes a Holding company, LLC Subsidiary​, Corporate Financial Program and an Estate Plan.

PROGRAM 2 Owner use up to 3 weeks 40% of Adjusted Gross Standard FF&E in high season & 3 weeks Revenues from the Unit and accessory in low season package required.PROGRAM 3 Owner use up to 6 weeks 30% of Adjusted Gross Standard FF&E in high season & 6 weeks Revenues from the Unit and accessory in low season package required.HIGH SEASON: DECEMBER 21st - APRIL 15th LOW SEASON: APRIL 16th - DECEMBER 20thNote: The following fees are deducted from the gross revenue before the split:5% Management fee, 5% Travel Agent Commissions, 2% Credit Card Commissions, $4.00 per occupiedroom night (TRUMP Fee) & Group meeting fee may apply.Other Monthly Fees: 4% of the gross revenue is moved to the FF&E Reserve account and approximately$20 for liability insurance.Monthly Condominium Dues: $895.57 (These can be deducted from your monthly revenue)Initial Rental Program enrollment fee $500 and $2500 initial FF&E Reserve account contribution.Fees for OWNERS STAYS: In Rental Program (Optional): 1

@Mary AinsworthFor my flipping business, I prefer to use fewer software programs to streamline things.

This criteria is for 1-4 and 5-8 unit programs.

There are lots of paid software programs that do this for you as well.