The cost to repair your vehicle, and perhaps the other person's car, will be WAY MORE than the cost of the insurance premiums you saved by not having insurance. 

Are there certain red flags that have saved you from a bad lease before?

(Granted, I am not factoring in various fees that may be saved by financing at acquisition).

Despite being assured that there would be significant tax savings on my 2023 taxes, there were no cost savings or advantages to having paid $5,000 for strategy in that tax year.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

I agree with @Nicholas L. and you, that 99 out 100 people who try this won't make daily home runs and won't retire in Bahamas.

Right now, I am not as interested in investing as I am in helping another investor in order to get some hands-on experience while my wife and I save a little bit more money.

In that case you might save taxes building with them.

I have a large lump sum saved in an investment account for down-payment and any additional costs.

so if you don't have a lot of money, then you'll have to save some up.hope this helps