I was at times doubting if I really need to spend $2000 on external measures but your post as well as several others has led me to believe the external stuff is essential.

If you go by financial metrics you're essentially filtering what you see by someone elses underwriting while disregarding the property itself. 

So having a diverse retirement plan is essential.

However, there have been times that (note that this is always novice investors) will send me endless listings and property addresses and ask me to call agents, drive by for them, do video walk throughs, etc; essentially invest many, many hours on their behalf, only to find out that they've bought a property either with another agent or off market in order to save money (ie; not pay me for my time and expertise after I've educated them on our market).

Maybe I would have had the wit to do what it said, maybe I wouldn't, but at least I would have had a shot.I would say the very largest challenge for someone starting out is fully understanding that the first 13 years of school, K-12, are essentially glorified babysitting in an enforced propaganda daycamp.

This is really basic stuff for most of you but I gotta ask...For someone who is just starting out and is looking to buy their first property, should I be looking to essentially get financing with high monthly payments in order to pay off the property and build equity ASAP or low monthly payments to try to generate as much cash flow.

I have a rental in Chicago that doesn't cash flow (was a prior residence I didn't buy it as such) but I keep it because I put in about $100/month roughly and my mortgage is being paid down essentially by someone else, I know it will appreciate and if my income were lower I could take the loss against my W-2 income.

Hyman Minsky was an economics professor who coined the, "Financial instability hypothesis", which essentially says that stability itself is destabilizing. 

say A and B are essentially identical neighboring properties but B has a 80% LTV mortgage on it so its costs are say 70% higher than A. 

We got a duplex essentially 0 down, we offered $5k down owner financing, bought over market value (full asking price), cash advanced a credit card to pay for the down and closing costs, cash flowed every month and eventually raised the rents (to increase the value of the property) and sold it, making around $70k after cashflow and profit selling in a few years - essentially we created money out of thin air.