I would base this first off of where I want to work first.

After doing some research on the ‘director,’ Kory, he’s actually just a freelance/self-employed salesman based in Utah… I should have sniffed it out earlier in the process than I did because even in the 1stinterview, some of the early questions from the screener included how much money I make, how much I have in my bank accounts, my credit score, how much credit card debt I have, and what my credit card limits are…I was then asked if I was willing to ‘leverage my credit’ aka max out my credit cards to be successful.

I'd be happy to have a conversation about good investment strategies for this area based on what you're looking for.

I'm here because I don't understand and I'm coming in with assumptions based on my own taxes over the years and you've kind of put me down or made fun of me for being "surprised" at how the tax law works.  

Based on the information in your profile, it seems likely that this is your one rental property although you mention in your profile that you also let out rooms in your own home.Out of your four options I think the worst is No. 4.

It will cost approx $4000 to remove the Oak tree based on a professional estimate.

Most of the software I use for deals for myself and my clients use an algorithm that will use statistical amounts for replacement based on current costs.

I would look into a DSCR loan option it will require 15-25% down depending on the lender but it's based off the asset and if it debt services rather than based off the individual. 

However, if you work with insurers based in Northern NJ you will have no trouble finding something that works. 2-4 unit properties are in abundance here and are often being house-hacked. 

This will go easier with water-based than with oil-based poly.