I'm being required to pay another application fee and then $600 application fee to hopefully get this approved by the Board to allow me to continue running the STR that they approved 6+ months ago. 

The vast majority of properties at their available prices will not meet this requirement.  

A big reason is the OO requirement to rent the JADU as its own unit,good luck

We have 2 San Antonio sub2 deals that are turn key homes and only require about $20-25k to close (assignment fee + closing costs).They're a great option!

The last few years have been great for investors/homebuyers who bought pre-con, but looking back to the few years after the 2014/15 boom, this wasn't the case, where many had actually committed to buying a property that wasn't quite worth what they signed up for closer to closing because the appraisal weren't matching the contract price, requiring a cash top-up.

For the BRRR method, houses that just require lighter work and have working utilities can be low hanging fruit and competitive.

Commercial deals are going to look at your qualifications as an investor as well as the DSCR value of the property supporting itself (at least here in the USA).For construction, you will need to look into licensing requirements such as a GC license.

As Jay mentioned they must be NMLS licensed if owner occupant of in several states even commercial needs licensing.The NMLS is like the database, each state has a division of banking that oversees lending requirements then you also on the federal level have CFPB as well as consumer protection laws.I want to add that I believe yesterday the CFPB is undergoing changes, but if it goes away that does not mean that many of the laws in place especially consumer protection laws would go away. 

It's a more involved discussion that requires one on one communication and no, joining a "community" does not prepare you.

One of the biggest challenges for everyone involved is being on the same page about the actual time required for maintenance.DIY landlords rarely properly track their time when it comes to property management in general - tracking their true time invested in maintenance is where they perform the worst.Investors that hire PMCs are rarely any better at understanding the true amount of time maintenance takes.