They supposedly have been living somewhere for 1 year and produced a letter from their landlord singing their praises of what great tenants they are  (which we all know anyone could have written). 

But something must have happened in the market to change the returns DSTs are producing.

What do you think the best possible experience an investor can have that reduces the "sifting through sooo much information" problem, quickly plugs them into a model such as one you've built and ultimately produces a transaction? 

If you are producing "real" cashflow of 200 per month, this should already have vacancy, capx, and maintenance factored into which indicates that there should be reserves and accounts created that will pay for these eventual problems. 

I was tending to make decisions based on how much “net income” was produced rather than increases in my wealth, or estate value.  

I can consider being a little more aggressive with a 401K as I have a defined benefit vested pension as well.Personally I wouldn't do it for a flip, but would consider it for a dividend producing (i.e rental income) property I would hold.I also wouldn't cash the whole thing out.

On the executive leases, they are essentially mid-term leases, and can produce 5-7k per month in North Central. 

The end result may not be very profitable for the owner, because the management company takes a large comp cut, but for analysis purposes the gross rental numbers they produce are significant, and they are NOT captured by AirDNA or other similar services.

As long as it is not your primary residence, it is used to produce income and you pay for a cost segregation study; yes, you can do it.

Because I like to have cash until it can produce return, I would not choose option 1 but the numbers do not show option 1 to be significantly worse than the other options.