I feel very confident that under the tutelage of @Lucas Carl I will continue to be successful.

You could house hack one of these but without the appreciation acquired over time or the value add, your profit will be consumed at selling.I agree with @Nick Foster on get to know the area before purchase but I also think that it takes at least 5 years (without a value add) of ownership to have a decent chance of being financially better than having rented (due to the selling costs and the likely negative initial cash flow).Rent. 

So all in all once I add a closing attorney to my team I'm fairly confident that me and my team can make this happen.

I’d like to try and require a deposit from guest directly now with a credit card, as I have no confidence in Airbnb’s protection system.

I would much rather buy a 4 unit (residential loan terms) and then another, until you're more confident to get, say, a 12 unit or larger. 

Are you confident it will?

Down payment will likely be 25% not 20% due to it being duplexesHow confident are you on the area and the rehab costs?

I am confident that there are multiple investors in your market that could use your computer background to their advantage.

You're pretty confident that 3 of the 4 major hotel/motels will have several feet or more of water on their ground level floor for the next few days. 

Therefore, when you start paying for marketing you can manage them better and have the confidence to convert at a high rate.