My plan is to funnel the rental incomes from all three properties, along with my W2 income, back into the HELOC while covering all expenses from it as well.

Getting a property with a partner / friend will not help you from getting hosed on taxes.I wouldn't move forward - You mentioned beng a high income earner so your hourly rate is very high.

Insurance-  we had 18 months of full lost income coverage.  

I was looking at DSCR loans because they don't require extensive checks like the bank loans and they "only" look at the income generated from the property to qualify for the loan.

One thing to be aware of is the FHA multifamily self-sufficiency calculation which determines if a property can generate enough rental income to cover its mortgage payments.

DSCR loans won't use your income to underwrite the loan.

Since my adjusted basis is about 50K, am I going to have a $250K gain on my income taxes this year?

.- Builds long-term wealth - Generates rental income - Increases equityCons.- Complex process - Requires financing - Dependent on market conditionsAirbnb:Pros.- Potential for higher returns - Flexible pricing - Short-term commitmentCons.- Requires active management - Subject to regulatory risks - Income can vary seasonallyI wish you the best in your new venture.

--> Passive income doesnt mean tax free income.

This could help decide if the income is enough.