Understanding how to properly outsource, how to deal with buyers (this was my first purchase, flip & listing).

Plumbing Check: Run water in all faucets ensure draining properly and no leaks.

I believe that any time is a good time to invest as long as the property checks out and cash flows properly.

I'm not opposed to setting up my books properly from now on, but am afraid it combined with the late filing will trigger an audit. 

It will still shield liability, if properly setup, and as long as your actions don't "pierce the corporate veil".  

It's possible that the proper operator could double or triple the income of a previous operator if done right (or if they were doing it wrong). 

Unless there's some extenuating circumstance (you're a GC, you're an agent etc) you should deal with as many business resources as you can and you definitely should not be using private money from inexperienced investors until you know how to handle it properly.

. :)If you have the right builder and proper contracts and specs you shouldn’t need to hire anyone to do this.  

Then I was so excited when it came back around that I lost my mind and didn't do the proper due diligence.

HOA fees can add up and you need to make sure it is properly managed.