Deductible: This is not a coverage but rather your portion of a claim.

I would like to add my car to the LLC as an asset, but i have heard several stores about this.Can I do that or not, and if so, do i deduct the interest on my car loan as "other interest" on schedule E or C?

I'm not a tax advisor (see your own personal tax advisor/CPA), but don't forget to take into account the new tax law is not supposed to allow for deductions for HELOC's any more save for a few circumstances.

Looking for someone who know the insides and outs of all the deductions I can take to capitalize on my investments.

You can't deduct them as expenses since the properties are not in service.You should speak to your accountant about the $$$s.

If so, it seems to me that you are filing these as taxes paid by you as a business deduction.

Term: 10 years, no balloon.Specifically, how would the taxes be applied and would only a portion or all of the acquisition and rehab expenses be able to be deducted?

I'm no tax accountant, but I believe either choice, the shade or the gift card, is tax deductible.

You can write off the investment related interest even if it is funded by the Heloc.But if you will take standard deduction, it doesn’t matter.If your itemized deduction were greater than standard deduction (24k if married in 2018), you could deduct the interest you paid on the heloc to the extent of your net investment income. 

Sec 199A deduction might come into play for you as well on your personal tax return.Seems like it might accomplish much of what you want.