I know that my current cash flow is a result of the unit being my primary residence first, and that not all units will cash flow like this, but can't help the feeling that I should be expanding my rental portfolio over the years.

If you don't own a primary residence I'd start there.

If the LLC and its income are entirely outside California, it typically does not require registration with the California Secretary of State (SOS) or payment of California Franchise Tax Board (FTB) fees, even if you reside in California.

Since you and your partner are unmarried and own a primary residence together, tax treatment of deductions (e.g., mortgage interest and property taxes) requires careful allocation.

Our current plan is to purchase our first home and live in it for 2-4 years before moving to a new home and using this first property as a rental, so my fiance and I are currently in the market for a home that we could use as our residence during the offseason and then use as a short term rental or something like that while we are away for 6-7 months.

You can print this one on your computer, no need for the “official” printed forms.W-9 asks them to enter their name, address, and tax ID – which can be a SSN, ITIN (for people who are not permanent residents) or EIN (business tax ID).

I am pretty sure you can not do a 1031 and use the proceeds to do anything to a primary residence.

Interest rates and cap rates change, competition changes, your PM ends up being horrible, lots of variables.Just to throw you a monkey wrench, in your killer spreadsheet does it include the credit score, income, and employer of every resident? 

It is also possible that either the folks in charge of the station, or the prosecutor have set a policy of not wanting to pursue non violent crimes, or even not paying attention to crimes against folks who are not local residents. 

I was looking for some advice (viable target areas in Cleveland or Ohio in general, financing options and credible PM/realtor contacts) from the experts here though especially if you are in a similar boat as mine (reside in Canada/Ontario area and invest in US).