I have done cash out refinances many times with properties held in corporations, and the proceeds are not considered taxable.

An individual is entitled to the same deductions as an entity.You may want to consider firing him.Net Rental Taxable income = Gross Rental Income - Rental Expenses

Cash out refinances are generally not taxable events. 

Later, capital can be returned to the owner as an 'ownership draw' and such a draw is not a taxable event.Rent is a business expense for company #1 and would be income for #2.

- If I purchase the next property, do I base the "taxable" portion on the GAIN of the house (i.e. the 150-175k in profit) or is it based on the total cost of the house?

@Chris Pa loans are not taxable.

Additionally, I can conduct a cost segregation study and take a massive bonus depreciation the first year, which will reduce my taxable income.

If you buy a large property (say 100 acres) for $100K, and sell a few small parcels from it totaling 20 acres for $60K overall, do you have to pay any taxes on the sale or would that still be considered non taxable since you haven’t realized a gain over the initial $100K purchase price (even though you still maintain possession of a majority of the land purchased)?

HSA deduction and standard deduction would give me taxable income of around 35k.

My question is, if I do incur a loss on the property can I just claim it on at 1040 form or will It just lower my personal W2 taxable income?