@Matt LeberYou're mixing together two completely unrelated taxes: IRS income taxes and local property taxes.

Any tax benefit for havingnegative cash flow i.e let say you have rentals with +ve cash flow that add the total income and for me i already have w2 so that extra +ve cash flow make me pay more to uncle SAM (which i don't mind as such, Uncle SAM can use that to fix the roads i travel) will -ve cash flow properties will negete the +ve cash flow with a long term goal that at some point the -ve cash flow will become +ve and i pay uncle SAM more to fix the road due to rain. is that your thinking too :)

This is because it’s the fastest way to achieve $1500-$2000/ month passive (when I’ll be 25 years old) which will also give me a HELOC, allow me the option to leave my job and get a less strenuous one, and be able to provide to my family and repeat the process but a lot faster.

You can use Heloc money for a down payment on investment property, but this loan will factor into your debt to income ratio. 

My theory is that not too many people want to buy them - the people living in those areas don't have a high enough income, credit score etc to purchase at 7% interest rates and it's investors who have a high risk tolerance who will buy them (like me and I don't have a high risk tolerance, just made a bad decision). 

This was done to protect senior citizens on fixed incomes from being forced to sell their homes due to unaffordable property tax increases.Since the passing of this amendment, all properties in Michigan have two property tax values associated with them:State Equalized Value (SEV): supposedly equal to 50% of the market value of a property, not based on recent sales price.Taxable Value: the SEV annually capped as long as there is not a transfer of ownership.City Assessors are charged with determining how much property values have changed each year.

Lenders will use your tax returns schedule E to calculate your monthly rental income.

I'm looking for some resources where I can learn how to properly analyze deals, especially larger and more complicated deals with multiple sources of financing, multiple tiers of investors, rental income to consider, vacancy rates, etc.

Good thing about personal loans is there is no LTV/CLTV involved its based off off income and credit.

My wife and I don't want to jeopardize our current mortgage (our children have no income), and we are worried that going through with this HELOC might cause our lender to see that our children are now on the deed, thereby invalidating our current mortgage and causing problems with the HELOC as well.