As you grow, its all about taking advantage of all the tax deductions you can. 

I’d like to know what tax preparations we could begin to consider now in order to ensure we can deduct a portion of improvements made to the shared living areas come tax season 2021. 

As far as I know, windows are considered structural, and depreciate on a 27.5 year schedule, but other things that are 'personal/tangible property, like carpeting, furniture, appliances, fixtures, etc. depreciate on a 5 year schedule and are eligible for first year 100% bonus depreciation, allowing you to take the deduction in the first year.When is it most beneficial? 

Do you want the loan, that is the interest deduction, to be against your primary residence or your rental? 

And from my understanding you are correct in assuming a deductible tax expense if you are “losing” money by paying more into mortgage.

Seeing as how I was referred to this lender by another who doesn't service FL and was fully aware of my tax history (6 figure deductions, etc.)

@Peter McDonough Would I still be able to take advantage of tax deductions from ordinary and necessary business expenses without having an LLC, but simply by owning investment properties?

since the property is paid off, i only pay for and deduct the property tax, hoa  and depreciation.can i- claim the property as a second home instead, stop taking depreciation and stop reporting the below market rent as income? 

Meaning, am I able to deduct all $20,000 (8k + 12k) from my taxes ?

If you make your own internal deductions (and you guys agree) for the tax that you pay on the profit, you can probably just send the money to your friend and avoid the legal entity stuff...As always, talk to a professional.