This is especially the case if you downsize from a house to a condo or townhouse because, not only would the space be smaller, but because HOA’s tend to take care of exterior care.

Doesn't come with land like an SFH.Id be subject to an HOA that can change policy/ raise fees at any time.Pros:Waterfront space is a scarce resource which could lead to better long term appreciation.

The neighbors commented to the buyers during the inspection that they were the nicest girls and were doing so well with their goals (one was learning to walk all the time instead of crawling at age ten.) 

If you renew them their renters insurance may continue to pay you rent and pay for their hotel space?

It will also require much more work than just making two livable spaces.

Same thing for a family of 3 renting a 2/1… new baby… need more space.  

You are definitely in the right space to continue learning and getting started with real estate investing.

So if there's a property A, worth 500k; and generating 10k cashflow; property B is worth 800k and generating 15k cashflow positive; I'd still go for property B.I didn't include SFH because I don't need to buy a super large house and not be able to rent any part of it (I am not keen renting it room by room or sharing common spaces).

Also, does anyone know if these policies cover if you are renting out the space or not?

All:  How would you compare the relative security (of your investment) for a warehouse/logistics center with office space with a national tenant like OfficeMax, Staples, or similar with a NNN lease with several years left and renew options; vs. a large 100-200 unit multi-family with decent occupancy in a good area?