Option 1 - NOI = Rent - (maintenance, vacancy, management, property tax, insurance)or Option 2NOI = Rent - (property tax, insurance)in both cases i assume DSCR = monthly payment/NOI

Medford also just voted to increase property taxes which is another reason to act. 

Oregon Tax Burden and politics have done me in :) 6.

In order to defer all of the tax you must purchase a replacement property that is at least as much or greater than what you are selling for.

Also, the tax benefits of the buy and holds help offset the increased tax consequences of fix and flips.

However, because the Department of the Treasury recognizes that reporting companies may need additional time to comply given the period when the preliminary injunction had been in effect, we have extended the reporting deadline as follows:Reporting companies that were created or registered prior to January 1, 2024 have until January 13, 2025 to file their initial beneficial ownership information reports with FinCEN.

One other possibility to prepare for is that the court may ask the two of you to meet with a mediator prior to the judge hearing the case.

I haven’t made any profit yet and I’m wondering if I should still file taxes for my “business “. 

You are a high w2 earner, The house is worth 110k today, you are buying from your grandma for 60k in exchange for free rent for life, upside ARV of 200k.The costs of owning the house will help provide tax relief on your high w2 earnings, you are buying a great chunk of equity that will pay off in the future, and you and your grandma are doing each other solids. 

It is amazing how many times I have seen the cash flow represented as rent - PITI and to compound the issue they did not realize the ADU would increase their property tax.