So, why would you NOT factor in a car payment when determining the liklihood of an applicant paying their rent consistently on time?

Cash Flow vs Buy and Hold, etc...That can help determine areas to invest, as some areas are better for cash flow and don't appreciate that much.

There are several things that come into play with determining if a property sale is capital gains or ordinary income. 

Not sure how long it's been vacant, but definitely have an Inspection done for any foundation issues, walk the property with a licensed GC to determine the exact SOW.

When you buy determines your short/long term capital gains.The "in-service" date = The point in time when you can start taking depreciation from.

As an investor you should not be relying on the realtor selling you a property as the sole factor in determining it's market rental rate. 

Once you complete their application process, they will determine you don't fall under their top tier borrower qualifications and propose terms that are far less favorable.

At any rate, I will need to determine if I am OK with negative cash flow for likely 6-12 months before being able to raise to market rent(and even still may be near break-even or negative depending on expense/capex calculations).I will have to re-read your post a few times to make sure I comprehend it all.

What’s the best way to determine which option is more valuable in the long run?

The Department of Housing and Urban Development (HUD) relies on comprehensive statistical data to determine the fair market rent (FMR) for regions across the U.S.