Tax season is in full swing, and for most individual taxpayers, the looming deadline for filing and payment is Monday, April 18, 2022.

@Joel OhA taxpayer renting a "dwelling unit", such as a house, apartment, condominium, mobile home, or boat on a short-term basis, from a single room to the entire property, typically reports the rental activity in their individual tax return on Schedule E.

To qualify as a real estate professional, a taxpayer must meet the following two criteria (IRC Sec. 469(c)(7)(B):More than one-half of the personal services performed in all trades or businesses by the taxpayer during such taxable year are performed in real property trades or businesses in which the taxpayer materially participates, andSuch taxpayer performs more than 750 hours of services during the tax year in real property trades or businesses in which the taxpayer participates.You must also meet material participation requirements for each rental (or group the activity). 

@Lane Kawaoka"willing to check the box"...a little dangerous...The taxpayer is ultimately responsible for what's on their return. 

I have seen to many people try to do taxes themselves and then we have to go back 3 years and amend the returns because the taxpayer either is exposing themselves to audit risk or missed out on a great deduction that would have resulted in a larger refund 

@Nick Mercurio Property tax payments are usually due twice a year, payable before the due date.

., cleaning, restocking, shopping for stocked items, maintenance, billing), the Taxpayer would have a hard time proving no one had more time spent on the business. 

I will need to use my money to make Mortgage, Insurance and Tax payments on it until I can get it with a Vacation Rental company (I use Vacasa)  I have a good job making over 6 digits that I plan to keep working at for another 5 years unless I sell this house and do really well which is highly possible from my experience unless the market tanks similar to 2008. 

Remember that about half of loans are backed by insurance (you and me as the tax payer) so there is money on the "back end" that the bank stands to gain as well.

When an IRA engages in a trade or business on a regular or repeated basis (which frequent flipping becomes) then the IRA is subject to taxation called UBTI meant to level the playing field for tax-paying business and protect them from unfair competition.So, generally an IRA is better suited to truly passive investments like holding rentals, private lending (such as to unrelated flippers), and syndications.