Am I better suited getting into a multi-family or a single family home and look at potentially adding value somehow? 

Everything looks correct here for me except for potentially one thing.

HOA now will be allowing max 3 rentals per year, which they say avoids the potential "grandfathering" issue.  

This is a lawyer questions because you can't generally pay a fee. 

EXAMPLE:  These are fictional numbers, as I don't know your market.Shared Residence: $600 EACH room = $3000 GROSS POTENTIALSingle Family:  $2300 GROSS POTENTIAL RENTDuPlex:  $1500 PER UNIT = $3000 GROSS POTENTIAL 

I want to purchase a condo with the loan 100% in my name, with the intention of completely remodeling the unit for potential rental opportunity. 

I have posted before about the desire to own land and potentially have a spot where I could decompress and relax in the offseason.

D) which of these two strategies would have the better resale potential?

Keep in mind as well that many lawyers even some real estate lawyers won't be familiar enough with the issues commonly found with these kinds of purchases.

@Patrick Fraire if I could overlay that with properties for sale that would be awesome, unfortunately its super time consuming to flip back and forth between the Riverside map and a map of properties for sale (and many of the potentially interesting ones are right near the borders).