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?!

Many investor's from NYC, Toronto, DC, Florida, California and internationally are investing here in Buffalo NY. 

At my place of work they offer vanguard funds which charge 0.04% for US index funds and about 0.14% for international index funds.

I interned at one of the greatest Emergency Management Companies and I have every but three certifications you could have in the fire service.

They do this for a living, come from families that do this for a living, have generational wealth and/or are syndicating deals out to domestic and international investors.

After all, for the Professionals, we use Future Value (FV), Discounted Cash Flows (DCF), Internal Rates of Return (IRR), Net Present Values (NPV), etc. in our calculations.