Can anyone talk about the immediate differences, what surprised them the most or what red flags to look out for?

With double title insurance fees and transfer taxes, it could easily put you into the red. 

We had lots of showing, and rented one of the units very quick (although there was some red flags we ignored in our tenant screeening, which eventually lead to having to evict them).  

@Bryan Cohenas already mentioned the term is Quit Claim Deed, not "Quick"Generally a quit claim deed is a red flag.

All signs point to a red hot market in St Peterburg, Clearwater, and elsewhere in Pinellas County Florida and the Tampa Bay region for 2016 in this Jan 2016 Market Status from Pinellas Realtor Organization.Some highlights:The new year started strong for Pinellas County real estate, with January 2016 stats showing more new listings, fewer days on market, and Median Sale Prices way up from January 2015. 

Would the cashier's check raise a red flag for you?

If you can get a property along or near the Blue or Red lines you should be in good shape, but they will cost more.

From a lending perspective, is this a true red flag for a lender?  

RED FLAG

I'm sure you have already, but if not checkout meetup.com for some REI meetups in Red Deer as well.Best of luck getting you're investing career started Daniel!