A lender that mostly does white picket fence FTHB type math isn't going to cut it. 

They take nearly their entire cut off the top, so it's against their business interest to pay to collect on it.

The bottom line is that I lack the knowledge of how one goes about cutting down on the actual amounts the City wants - no one ever goes into detail about the execution. 

My mortgage payment was cut in half and I am presently bringing in 500.00 passive income. 

I would look into Self Directed IRA or 401K, both of those tools can drastically cut the time between "saving money" to "purchasing a property".  

I can see a ton on the web, but don't know if there is something that generally stands out in the real estate community as a cut above. 

Wanted to get some ideas on how I can incentivize him to be motivated to get the job done for as low as possible without obviously cutting corners.

You have a edge over someone who's not tech savy.

Do not cut any corners on a prospective deal to make it look better.Always do the math analysis and try to look at the prospective property before you submit an offer or at least have a clause in the sales contract that allows you some time (about 10 days) to make a detailed inspection without having a penalty that will hurt you too much.  

That means either more work for me or management, which cuts further into cash flow.Brian