Getting into multi families is a great investment strategy.

Initially, we thought we’d buy a condo in Rogers Park and then list it on AirBnB when we weren’t there, but it looks like AirBnb laws make this strategy complicated.

You can find discussions about strategy, running numbers, creating spreadsheets, and real life problems investors run into.

.- The most important exercise would also be to figure out exit strategy.

Complete diligent under writing, be confident in your numbers and you asset strategy then close the deal.

My advice starting out is stick to your lead generation strategies and don't discouraged in the beginning.

Best bet for rental is Baltimore county (try buying houses built after 1978 to avoid dealing with lead abatement laws.

You can do well here with STR and even mid-term rentals, so if you're looking for a market that would allow you to explore those strategies in the future or diversify your portfolio, this could be it. 

My strategy at this moment: Buy land with a 5% down conventional loan that will allow the construction of an all adobe brick four-plex. 

Pensacola FloridaLocal bank/ credit union will probably be your best bet, or a commercial mortgage broker.