My question is: if we decide to pull the trigger on this deal what are some creative strategies to optimize my return on this land?

-Determine a financing strategy-Set my budget-Determine 3 key target markets to focus onSpecific questions I need to get solid answers for:- What is an optimal financing strategy to get me to 10 units in the shortest period of time? 

The most important thing to look at is the historical operation of the property, then factor in the expense ratios or nearby properties, consider the differed maintenance, age of building, class of building and other operational expenses you may add or subtract to optimize NOI

The white balance of his camera will be more optimized, contrast and levels will be better judged by the camera's software, even the focus will be sharper if you flood the rooms with light.

I made my first offer on a house I can barely afford as a primary resident (3bd, 1.5ba close to Tufts University), I am glad the owners went with another offer, I would of paid close to 2.5k a month in "rent" for a single room assuming I rented out the other rooms at a near optimal price.

I'm not a huge fan of the psychological impact of this as you get a big lump of money and it tends to make us feel 'we need to invest this ASAP' - which isn't optimal IMO.The above I'm told will often work under the traditional 'retail' arm of most banks. 

Is that an optimal strategy?

I'm also considering SFH but those are extremely difficult to find turnkey and a good price for the math above for optimal net profit.

@Jacob Breazile when you live in an expensive real estate market cash flow is very rarely going to be optimal in our current phase of the market, so you're left with a couple of options.1. take the lower cash flow.2. invest in a different market. 

Discuss your portfolio and come up with a strategy with an attorney *who has real estate investing experience*    -  Sure other attorneys can help, but they often don't know the niche ways to optimize these entities.