2) What are the seasonal effects on real estate?

@Sushil IyerWith my experience, to analyze properties effectively, you can start with resources like MLS listings, Crexi/Loopnet, tax assessor websites, or paid tools like Costar and Reonomy.

One thing to watch out for is the financing aspect of it - could be a hurdle getting a loan if the transaction is "non-arms length" - i.e. between "Friends" - might be worth looking at seller financing too

How do I design a small yet effective real estate portfolio?

My thought is is use the Rent Ready feature of reporting his payment history to the credit bureau so it can work in his favor as a trade line, but I'm wondering if this is an unnecessary added step since he can already pull transactions on his bank side. 

And asking an agent to run comps on 50 properties a day isn't effective.

So 1031 effectively reset the qualified/non-quaified use of prior owned property.

Though fee schedules vary by company, generally speaking, you'll pay more up front for checkbook control and less over time, since the full custodial companies will have transaction fees not to mention the red tape of going through the custodian for all transactions. 

I was mainly thinking about the effects of putting an entire strong cashflow back into the mortgage.

Thanks Canopy Title is great with assignments and wholesale transactions!