He pays the rent every month (early you said) and is being proactive to ensure he can continue to pay his rent. 

In this day in age, there are so many ways to get the data from the MLS for free that there is no reason to be an agent just to get it.

This ensures it is done. 

Calculate on current market data, anything on that can be the "cherry on top".

The market may be headed for a downturn, but recent data does not support that thesis, at least not in the near term.

At my brokerage, we require investors agree to an initial meeting with us prior to sending them our properties to ensure safety, full disclosure, and full transparency. 

Also with amazon moving next door thas gonna ripple into the CT housing economy (just a guess no data for that one).

To successfully perform a flip the house flipping company needs to Spend time & money marketing to distressed sellers to source a deal with a large profit potentialEstimate the ARV of the dealEstimate the repair costs of the dealDetermine if there is enough profit in the deal to make sense for a flipNegotiate a sales price with the owner of the propertyHire the General ContractorManage the renovationEnsure the renovation is completed on time & on budgetMarket & sell the property for the estimated ARV to ensure they hit the estimated profit marginAfter successfully doing all of that why would they then hand over the majority of the profits to you?

If it intimidates you, don't worry, I will attempt to be concise and provide a laymens terms summary.Basic statistics crash course:Obtain as many sample rent data as possible (Zillow works)Define alpha for null hypothesis testing ( 0.05)Run multiple regression analysis (#bed, #bath, sq ft) against active rental list prices.Observe P-values for each metricResult:#Bed - 0.02#Bath - 0.04Sq ft - 0.02All are below or equal to 0.05, reject null hypothesis (statistically significant).Create multiple regression line using coefficients for each metric.Input variables from project property and solve for rent!

No software is good at everything so you have to choose what's important to you:  Is it Data?