We are constantly looking at properties in different sub markets and need to understand if (as you said it) the subject property is trading at market, above or below and figure out if the price is right.

The quality of them PM is one thing, but it only gets amplified by the quality (or lack thereof) of the properties and the resulting quality of the tenants.If you were to illustrate this with math it would look like this:  0.1 x 0.1 x 0.1 = your result.The answer to your question is obvious, but frankly easier said than done: buy quality properties with few repairs, they will attract great tenants with few issues and even a mediocre PM will do just fine.The allure of cheap cash flowing properties is real: After I had invested all my original capital I bough a few cheaper properties in Milwaukee (this was around 2010, so they were really cheap) and fortunately traded out of them within a couple years - it taught me a lot!

If I just wanted to buy real estate at market value I would just buy into an exchange traded REIT or REIT mutual fund or ETF as a diversified portfolio of REITs should match inflation over the long term and provide increasing dividends.  

I am also a carpenter by trade in Local 291 and have been working in this field for a decade now).

Work on getting your "network" of trades (handyman/contractor, electrician, plumber, hvac, etc.) together so you can handle getting stuff repaired/replaced. 

However, the loan is generally more expensive, so it a trade off if you were going that way. 

I'd say that still stands in the better markets, but it's important to try to base your comps on deals that have traded in the past three months, especially in July/Aug/Sept, since those buyers and sales prices should be a real barometer of where pricing is at, since around May is when we slided into a slow-down. 

Same reason a 10 year treasury pays less than a BBB rated bond.Unless you live in a VERY pricy area, I'd strongly suggest trading a higher return for being closer to home.  

He is a handyman by trade, and has general liability insurance.

My crystal ball tells me, with lumber prices so high, labor shortages in the home building trades, we are not in a bubble.