I know that appreciation is a gamble, but if a city's economy is diversified and there is a finite amount of land in the prime location that is downtown/waterfront then chances are it should appreciate, right?

But of course that’s the gamble. 

On our own projects, we always make our own assessments of rental rates, and there are numerous resources for this data once you know where to look.You need to determine the business plan, i.e. duplexes vs. larger project, then have an architect layout the design on your chosen path, then run a set of number (proforma) to determine feasibility.

You see, I want to make my first purchase within the next 12 months, but I haven't actually chosen a region just yet. 

If I want to gamble I go to the casino.

If turns out to be a rental (which is my expectation) then I will bank the cashflow and work towards the BRRRR strategy to add another property in the near future.What I’ve been doing lately to make dreams realty:-Listened to one or two BP Podcasts a day-Spent tons of spare time on Zillow browsing properties-Identified a single family property that has real potential to be my first deal-Gotten an insurance quote and dug up tax records on the property-Talked to a couple area realtors and chosen one whose background and experience best fits my goals-Toured the property-Crunched tons of numbers based on different scenarios-Arranged a second showing for tomorrow, with a local contractor who will be joining me for the showing to provide a quote on the work that would be needed.I am super excited for tomorrow!

I'm utilizing both of those stock options and feel it is in line with my "gamble" on the company as a whole, if all goes well and they grow and show a profit, it will have been a great investment. 

If the Master policy is insured correctly then this should satisfy your lender, however, if the association has chosen to cut corners and is not fullying ensuring the property/building then your lender might require you to purchase flood insurance to balance the requirements of the loan.

I think I have got enough knowledge and capital to buy my first SFH or duplex rental property, but my wife thinks buying rental properties is gambling.

That is exactly what I see, buying condos from a wholeseller seems like a real gamble.