If he does not do the work he is supposed to do or do it in the timeframe that was initially anticipated, what happens?

Expecting inexpensive (cheap) property management to be competent 8.

It's an inexpensive market, but don't fall for cheap opportunities that look good on paper and details left out concerning the location and the vacancy rate.

-Taxes-Home insurance-Mortgage Insurance -Maintenance/Repairs-Capex-Vacancy-Property Management (many include this even if you don't plan on initially offloading to PM)-Utilities Let's say all in expenses are $2,000 per month for easy math purposes. 

The course being 6 months implies 3 deals are possible in that time frame yet I’ve asked time and again - has anyone done 3?

Although, as mentioned at the top, the pull chain switches are often a weak spot, however they are often easy to simply replace with an inexpensive, universal replacement switch from the hardware store.

I also include a timeframe (3 business days) that the lease needs to be signed and returned to me, once it is given to them or they can face a forfeiture of their holding deposit. 

The first time I went there I was surprised how underdeveloped and relatively inexpensive it is.

I wanted to reach out for advice / thoughts from other investors in expensive markets.

I understand what you're saying, I feel I didn't mention anything on time frames.