Stay away from Chicago unless you are required by your employer to live in Chicago. 

I currently own 1 SFH and 6 multis of various size the largest being 8 units.

@Mei Zhu We recently did a shower with tile to maximize the space because the surround that was available for the size took about 2” off per side making it really small.

Maybe a different way to go about it is evaluating the market rate for a rental of that size.  

Given your plans to use VA loans for multiple properties, it’s important to consider a few key factors when deciding on your next purchase.Since you’re already using a VA loan for the 2300 sqft home, it’s understandable to think about the size of your future properties.

Market OverviewThe Los Angeles apartment market is comprised of 864,197 units in thirty-seven geographic concentrations ranging in size from the 62,684 unit Hollywood/Silver Lake submarket to the Tujunga/La Crescenta/Montrose submarket, which amounts to 5,448 units.

Talk about how good the schools are, how close to the beaches or other attractions, Size/type of kitchen, ease of maintenance of swimming pool if in place or jet powered swim lane, Covered parking if so, etc. 

They sent a very professional slide pitch deck that showed all of their justifications around that specific market, e.g. employment market, housing shortage data, the new developments in the area, the air bnb data, etc. etc.They also stated the numbers were conservative (7 year to reach the target returns) and that likely it will be year 4-5.

It's great that you already have a home and potential ADU too since being self-employed in the arts can also have extra hurdles just getting approved for a loan. 

., and pick it up in three days, and in colors and sizes not picked by a homeowner, there is little or no bidding.