By then I wish to have a portfolio of short term rentals.I am in preliminary stages and am still narrowing down location based on where I would like to live in 5 years as well as location accessibility and demand.Listening to podcasts etc...

As an architect I use Sketchup for preliminary designs, presentation images, (Flythru's, client mtgs, etc.) 3D warehouse is a very useful tool to download components directly into SketchUp. 

I would definitely investigate further if you are looking for cash flow. 

Any quick back of the envelope calculations I should do to get starting figuring out if a deal is worthwhile to investigate?

(A recorded trustee's deed (or similar alternative) confirming the amount paid by the grantee to trustee may be substituted for a settlement statement if a settlement statement was not provided to the purchaser at time of sale.)The preliminary title search or report must confirm that there are no existing liens on the subject property.The sources of funds for the purchase transaction are documented (such as bank statements, personal loan documents, or a HELOC on another property).If the source of funds used to acquire the property was an unsecured loan or a loan secured by an asset other than the subject property (such as a HELOC secured by another property), the settlement statement for the refinance transaction must reflect that all cash-out proceeds be used to pay off or pay down, as applicable, the loan used to purchase the property.

I'm sure other people have more efficient methods, but this works for me as I like to inspect damn near every neighborhood of a city online and like to be very thorough in my investigations.

I totally agree with the possible problem scenarios and I'll investigate the possibility of renting additional parking!!!

Any pointers I have a real estate attorney I was going to walk in Wednesday and tell him these fiduciarys are being investigated by the IRS??

I'm just starting to investigate real estate investing, and as a frequent rider of NJ Transit, I'd think East Orange is a perfect place for investing. 

I am in escrow and have a preliminary title report dated May 1, 2017.