While it is true that the time of year can influence market activity, as others have mentioned, there is usually a trade-off depending on the season.

In the end, if the former is true, then lenders will value it as land with improvements.

if you add one ADU, you will likely be comped against quads with maybe a slight adjustment for it not being a true quad.  

But Im heavily lacking true mentorship to take me to my intended goal of reaching the financial independence community so I can continue to gain more of my freedom and time with loved ones!

If that is true, is there any reason not to start with multi family?

(insurance kills) Hey Alex, does this still hold true about minimum 20% down for dscrs

That's definitely true.

This means that the true Cash on Cash return would be 12-18% as opposed to the 30%+ that they advertise.  

This may or may not be true, but either way it sounds like your best move may be a court ordered payment plan.

@V.G Jason It is true that a duplex limits your rental pool.