However, my hold up is what market to look at that will help me meet my goals.

That will give me a gross profit of 20% minus holding and commissions.

Quote from @Andrew Lawlor: I've been actively investing in short-term rental properties for the past three years, managing one live property and another that will go live in two months.

its part of the game, work on getting better terms with time.

The bullet in the response that is standing out to me is:"(7) The accessory dwelling shall not be a short-term residential rental, as defined by City Code section 3-2-152(a)(2), for a period exceeding 120 days per calendar year."

@Desiree Board For your mix of long-term rentals (LTRs), short-term rentals (STRs), and house flipping, an LLC is ideal for liability protection and pass-through taxation.

We also just purchased a house in Oliver, WI that we plan to run as a short-term rental.

Not all homes are great long term rentals! 

Hi Randall-Congratulations on buying a rental property well back in 2020.I am sorry to hear the property is now cashflow negative $200 a month.Your question is should you sell or continue to keep it with the negative cashflow.Depends on your personal goals and if being negative $200 a month plus any unexpected repairs or vacancies is affordable to you, but if you can solve the negative cashflow by turning the property into a furnished mid-term rental, for example, your future self may thank you.To Your Success!

If it’s a structured settlement and you aren’t getting a lump lum, you could contribute some of that to a Roth or Traditional IRA each year, or if you are self employed even more to a SEP IRA.Also what’s your short term, mid term and long term objectives?