There are pros and cons for this approach and yes the Contractor and Architect would be on the same team and work in tandem.  

I know it is incredibly hard to drain that emergency fund.

I need advice on deciding what is the best approach for this situation.  

Best approach is to not invest in properties that do not have separately metered utilities.

Tip #3Network, network, network This tip will get you incredibly far.

As far as the home upsize or downsize process, there are innovators such as Dorrmat that is now providing ways to make the home buying process incredibly easy.

I've just never been in a big rush to lose money so that approach doesn't appeal to me personally. if you want to rent, and use your capital to buy a cash flow positive property, then that's not such a bad idea ;) 

From a viewpoint of maintaining W2 income to qualify for traditional financing I can understand it however when the ball is officially rolling and you have a fair amount of capital in your possession what has prevented you from taking the leap into a more full time and active approach to your investment dealings?

The daisy chain approach almost always ends up in a tremendous amount of your time being wasted, and the deal falling apart. 6.

If this is a repeated behaviour, you need to take a different approach.