Background: I am a Simulation Analyst (research, data analysis, computer modeling, etc) Not REI , trying my best to learn as we speak.Looking for buy & hold properties in Middlesex.What means for me is any data that I could use to predict if I am currently buying at the peak of the bell curve or the bottom.

To expand your toolbox, consider the following additional resources:(1) Cashflow Game (sometimes played at local real estate meetups)To test various strategies in a simulation environment, play some games conservatively and other games aggressively.

Look at their web sites and simulate a booking. 

We would like to set everything up as if it were long distance investing to simulate out-of-state if we eventually go that route. 

Yeah, I don't know whether in the next few years there will be a deflation, but with consideration of fed simulation and QE, there is also a good chance for inflation.

In large complexes you can stand out by having big amenities like pools, golf simulators, etc but in small complexes it’s only 2 parties so you do not get advantage of many people

When I questioned why his underwriters said they won't do simul closes.

Most nights you can find me racing simulated race cars against others from around the world 🏎

I've considered using a Monte Carlo Simulation method to assign a probability to each variable ( building sq.ft, lot size, finish quality, garage type, time of year sold, etc., etc) in order to mathematically understand the risk/reward of a project and contributions of each variable to such.

I can tell by your verbiage and questions you are out of comfort zone with this.It's best to follow the advice of your CPA and Attorney.You could ask your tax pro and attorney about:I assume these are both self employed sole proprietorships, vs legal entities (LLC, S-Corp, Corp).If so, why not just DBA and just do the work of both under that name.Sometimes when you shut down (legally wind up) a company you have an unexpected tax hit.To anylize the possible (LARGE or small or nothing) tax consequences, your tax pro might have to do a mock tax return and simulate that happening (and you pay for it), that way you would know if and how much a tax hit closing up would cause.[1]  It's best to follow the advice of your CPA and Attorney.[2]  It's best to follow the advice of your CPA and Attorney.[3]  It's best to follow the advice of your CPA and Attorney.There is also the credit history of both businesses to consider, if they rely on credit, will the credit availability of one business be enough to do the business of both.I don't think anyone online can give you advice that will work out for you without the possibility of great risk.It's best to follow the advice of your CPA and Attorney.Good Luck!