On the one that this thread is the subject of, all our internal people said "no Chris you can't do that" but it was done anyways.Yours, I was at least getting hesitant "well, in theory yes..." answers.

If you're able, find a strategy that interests you and seek to "intern" at it for a period.

You said that you learned a lot from real estate the last year, so my advice would be the following for your next step: make sure to connect with a more experienced investor and become an intern to do the jobs that he/she doesn't want to do, or apply for a position in a real estate agency in where you are from. 

I am planning to purchase my 1st MF  out of NYC area, and possibly rent by the room possibly to international students / college students.

It is very hard to establish at tribunal that the damage was done intentionally with malice and not just out of stupidity: case example; tenant brought motorbike into living room to change oil and severly damaged/stained carpet - judge ruled tenant had not set out intentionally to cause damage to the carpet -so this was not covered on the other hand, tenant caused offensive graffitti to internal walls -this was ruled to have been done intentionally with malice -so covered However, this policy comes into its own mainly for rent default, of varrying amounts depending on the circumstances but in some cases upto 12weeks if the tenant does a runner.

You're good at it, stick with it, and use your Wife's skill set to open more opportunities to do what you do.My Wife was an International Tax Consultant so she immediately took control of the books, expenses and all financial matters (Thank God!!).

It's internally consistent and rational, given that context. 

My broad stroke plan is STRs locally and then expanding internationally following getting my Italian citizenship (in the works).

The actual LLC registration is not difficult - it gets potentially difficult when you have partners and want to negotiate an operating agreement (the internal document governing  the LLC) - I think this is when you should speak with a lawyer.

You can't get away without learning how to calculate 10 year pro-forma Rates of Return.The calculations were done on both Stocks and Real Estate because it really doesn't matter.There is an investment of capital, there maybe some intermediate movement of cash flows, and then there is a return of that investment.Once you get all the cash flows, you just calculate an Internal Rate of Return (IRR).SIMPLE, right?!