When the second type of person tries to self-manage they end up frustrated and honestly making less money than they would if they found a property manager who actually does this full time, knows how to run an STR effectively, and just paid them to do it. 

Generally adding an ADU isn't worth it but the exception would be in high-density areas with housing crises'.

I'm a very conservative investor and may look through a hundred deals a month, and at the end of the year only invest in 4-5.

Is this what you want to offer to your renters going forward into the future until the end of service life of these units?

Get a CPA to get that advice.I highly suggest you don't cash out the retirement.

@Trevor Smith - Did you end up buying the multi in Northeastern?

I read through the rules on the HOA and it clearly states vacation rental guests can use the dock slip if I have one to provide them however I just want to make sure I'm setting it up properly so neighbors/other boat owners don't get upset with multiple guests each month using it if it ends up being a popular request.Anything helps!

Do you recommend that I start the process when the current tenant's lease ends, or when the tenant is still in the property?

If she's not happy with those terms, she's welcome to take the happy clause and this one time only, you will allow her to break her lease early if she's out by the end of the month. 

And I'm not just talking about the crazy high prices.