@Nick Mauldin : You simply ask for a T12 (YTD for 2017), Current rent roll, and a PNL for 2016 and 2015 (schedule E will suffice.)If this is a deal you sourced yourself by calling the primary, then they may be a little cagey about providing ALL of the above, but will often provide some of it.

They ultimately own the underlying property indirectly through the investment vehicleA, B, C, D, E form Partnership ABCDE.

If that is the case, creating a company to have the rental properties under the company will have the same effect - your loss from the rental properties will be reported on K-1 (instead of Schedule E), which will be subject to same limitations. 

There are lots of quantitative metrics ("mainstream" as you say) to observe here (P/E for the S&P - see chart below, margin levels, ratio of total market cap to GDP, etc), & anyone with access to google can see the same numbers.

Thanks for the response as well Paul, my concerns are not necessarily around depreciation (I’m pretty sure that buildings are depreciated over 27.5 years opposed to 20 years) or other deductions that are typical to long term rentals but rather tax guidance that dictates what is a schedule E rental portfolio vs. a schedule C business similar to hotels.  

That sounds strange, but you have nothing holding you back from venturing out of your security...because you have lost that security blanket that was your job.I would venture to say, that most of the success stories in history, started out where you are right now...me included.So, with nothing holding you back, and with plenty of time on your hands (time will always be your greatest asset...since you can never get it back), if you want to get into REI, you need to do the following:1 - Learn,2 - Learn some more,3 - Keep learning.Places to learn (before you say "that costs money"), that don't cost any money are:1 - Online education sites that have free articles written by experts in their fields.2 - Free e-books, that you can get online.3 - Joining your local REIC's to both learn and network.4 - ...and never stop learning...even when you become a success at this (and you will)Also, three very critical actions you MUST follow to be a success:1 - Always think possitive.2 - Train yourself to think of future "obstacles" as temporary problems...and you are the problem solver. 

Watch your deductions on your schedule E.

@Ryan E.

@Brian Karlow Sounds like you could tack a trespassing charge on to what @Stan Hill said about B&E. 

., an actual rentor in with a lease agreement is great documentation.Email conversations with your professionals strategizing on how to treat this property long term is also documentation.Getting the property on your Schedule E is pretty important as well.All of these things paint a picture.