Ideally 20k/month in passive income in locations that I know very well (Cleveland, AZ, OIB-NC and San Diego) and will not go beyond my area of expertise at this point. 

If you put together good systems you can avoid that somewhat, but I can say that I deal with more problems on my one property in a C class neighborhood than I do on all of my other properties (which are in B class areas) combined. 

I might be able to fill in the gaps so you can start looking for the ideal project. 

Ideally I would like to find a SFH (3/2 minimum) that I can turn into a rental in 1-2 years.

Ideally, you find a 3- or 4-family property.

Ideally, you build up a strong portfolio that will support your family in retirement.

Chase bank as auto-transfer amounts as well.

You can also get pretty close with overhead measurements from Google Earth, although math is required, and don't forget to subtract the garage, but ideally if you get to the point of making an offer you will have seen the house and/ or the owner will tell you how big it is.

Ideally, I would like to find a small multi-family to house hack, or even potentially a large single-family home. 

The alternative to turn key is not some ideal, guaranteed slam dunk goldmine.