Are there issues that you think you should avoid regardless of potential for discount? 

This defers capital gains and depreciation recapture taxes on the sale of your fourplex.After converting it into your primary residence, you may qualify for the primary residence capital gains exclusion ($250K single/$500K married), but only for appreciation after the conversion; gains from the rental period remain taxable.

It's very possible that whatever change might happen won't be in affect until 2026 also.It's also worth noting that any depreciation taken for the property for rental purposes doesn't become part of the Sec. 121 exclusion should you choose to take that in a future year.

I'm working with an investor client who is particularly interested in fix & flips. we've come across a number of lender owned / HUD owned properties with steep discounts.

I could quickly determine if I wanted to offer a discount or not.What I don't like is Pricelabs can swing pricing for certain nights by over $200 overnight.

Similarly, the sale ($575K) minus your adjusted basis determines your capital gain.You may qualify for the primary residence exclusion (up to $250K single/$500K married) if you lived there 2 of the last 5 years.

Hey @Kevin Brown, we use QuickBooks Online exclusively for all of our REI Clients.

Their insurance has asked me to return the month's payment for the remaining days of their rental (Unfortunately, I did not have a cancellation agreement).I am unsure how to handle this situation, especially since I couldn't fill the majority of the rental dates and had to offer discounts for the days I did manage to book.

Due to current interest rates, many CAP rates are much lower than they should be and usually there is only so much price discount a non-delinquent seller will be able or willing to offer.

This also depends on how are you calculate cash flow and what you're using to discount for expenses.