i've searched the forums and maybe i missed it, but don't see anything speaking directly to this point. 

Should I buy a Muli-family home that is very high quality and needs nothing done and has potential to convert the attic into another unit.

Just a heads up that Bruce Norris is speaking at SJREI on September 13th.

Generally speaking, if you are comparing "1 LLC and 5 properties in it" vs "1 series LLC and 5 series under it with one property per series," in theory, series sounds better.

From the property owners I am speaking to sellign their place they are quoting 70-90% occupancy rate, on some pretty nice/updated waterfront homes. 

I do stay away from airbnb because I have found I get a better quality of a renter from sites like VRBO.com and CHBO....but again AirBnB might be just perfect for you in addition to other sites. 

I thought the same thing as @Russell Brazil - the house will need to be enormous with unbelievable quality to get that in Rockville.

But Rehabs, regardless of the quality of your Pre-Purchase Inspection or the Contractor you hire to do the work always seem to need more extensive (costly) work once you start tearing things out.   

As our screening process has become more strict, our quality of tenant has improved dramatically.

But note that you'll end up with a different quality of tenant than if you picked a neighborhood with houses priced at $75,000.