However, I also think that a lot of people who set out to pursue this strategy miss the fact that it is literally a lifetime commitment to deferring taxes, which by definition means not realizing the gains.

@Khaled El Dorry This strategy is know as a consolidation exchange, and like what @Adam Bartomeo said a single buyer might be difficult to find.

Since your goal is lowering monthly payments for better cash flow, it might be worth focusing on reducing expenses elsewhere or exploring other investment strategies.

You can start by researching the market, connecting with other investors, understanding your strategy, and practicing your calculations (you can use BP calculators to help with this).

Implementing a value add strategy, which will raise rents and force appreciation has been an unfair advantage in just about any market condition. 

I guess my challenge right now is to define the strategy and balance all the factors, such as job and population growth (value increase), cashflow (demand & supply market, interest rate, property tax, maintenance cost), and risk control (insurance etc). 

A primary residence will most often provide more favorable loan terms so if you are willing to wait one year while you living in your new property and are comfortable with renting out your primary residence to a tenant, then getting something such as an FHA loan is a good strategy to minimize your upfront costs and hopefully get better loan terms.

I’d greatly appreciate any insights on tools, contacts, or strategies that could make this type of investment more manageable. 

If you want out, you have to either sell low enough where the numbers make sense or one of these other creative strategies.

Look at their marketing strategy.