Building those "muscles" of being investor take time but don't be discouraged as everyone's ramp up time is different.If you are truly lost then perhaps the best use of your time might be in finding an excellent property manager to handle everything on your behalf for at least a year.

But they just made some changes to the rules for commercially zoned properties that are much more restrictive from what I heard.See the following links for more info:Short Term RentalsOWNING SHORT TERM RENTALS IN NEW ORLEANSA Guide To Orleans Parish's New Short-Term Rental RulesHere are a couple of recent news articles:Weak enforcement of short-term rental rules could cost NOLA millionsNew Orleans council wants more muscle in fight against illegal short-term rentals

Kind of like the brain version of going through a sport's motion enough times for it to get stored into subconscious muscle memory.

During this time he should be spending at least a half an hour to an hour a day browsing zillow and analyzing deals to start building that muscle.

It then becomes muscle memory which will accelerate the time to take to analyze the deals. 

Also had a bad dispute on money in the end and caused unnecessary tension to this day. 2.

Also had a bad dispute on money in the end and caused unnecessary tension to this day. 2.

A lot of tension here but you seem very knowledgeable about how STR work already.

However, if you property manager is willing to cause tension in their relationship with you over a $50 late fee it might be time to find a new property manager. 

I feel like the fact there are shared kitchens and bathrooms mean extra tension between tenants.