I will be getting married this summer and not 100% decided whether I will keep it or sell...the numbers were great to live here, but look a little different/not as good when seen strictly as an investment...but the owner occupied financing is tempting to keep...some things like the bedroom layout (two private bedrooms, one of which is small) and a room that can be a third bedroom but must walk through make it not the most appealing rental to everyone, but I think I have had less than four months total vacancy over those years including trying to fill it over winter as well as a broken pipe during a vacancy...

In an equity investment, those remedies aren't as available if you follow the regulations, thus the distinction. 

Now, I did notice somewhere there is a reference to new regulations on capitalizing acquisition costs. 

Unfortunately, bank must follow certain regulations and meet global debt service ratio's. 

Since I really don't know much about the railroad industry, the first thing I would do is research what (if any) regulations exist regarding what can be transported via train through residential areas.Not only do you have the concern of kids playing on the tracks, but the potential of derailment with hazardous or flammable materials. 

You can run all the what ifs you like, you can have any opinion you like, but in reality, there are rules and regulations you'll be dealing with, they may not be logical to you or fit with your thinking but that becomes irrelevant in the reality of real estate.

I bought 3 houses around that time: one was a flip that failed and I immediately converted to a profitable rental, the second was strictly as a rental, and the third was a move-in rehab for a later sale.Then I wanted to get into multi-family, but got distracted and opened up a small retail space - which pretty much wrecked me.

(in most markets, your market may be different).Because of the MANY new lending regulations it can be hard to imposable for a buyer to get a owner occupied loan to buy your homes from you when you eventual liquidate. meaning you are selling to cash buyers and investors only.

Rules & regulations of the HOA board- Some may not allow rentals or they have rules regarding rentals.  3.  

The regulators don't like it, examiners don't like it and neither do state and federal entities.