I find myself contemplating the idea of finding mentors or coaches to help me get on my feet.

Have you spoken with other property managers in the area to get an idea of target rents?

The idea is to get is much out as low of tax rate as possible.

Single Family in Long Island  , 2000sf, asking price is 1.3....Idea is to expand home to 5500sf based on comps with a FMV of 2.3-2.5

You really should get some professional advice on how to properly operate your LLC. 

The idea is that you build a following of warm relationships and can leverage your reputation when you need a tenant.  

If we moved out and rented the main house as-is, we'd barely break even or even potentially enter negative cashflow.That's why the idea of renting out the ADU for extra income sounds appealing.

@Colleen Langdon That's a great idea!  

Does anyone have ideas of who to talk? 

So having a proper cap rate will be important to determining how we can increase value.