With a Conventional Loan you can buy a SFH, Duplex, Triplex or Quadplex with as little as 5% Down if it is your primary residence as long as you have the intention of occupying one of the units for 1 year after closing escrow.This is the strategy I have personally implemented and have assisted many of my investor clients in doing the same. 20% Down is also beneficial as it keeps your payment low but it does limit your ability of buying more real estate faster.i would be more than happy to discuss the different strategies with you over the phone or in person.

@Jeffrey Mair I would keep your rentals forever, especially that they are cash flowing. 

Personally, I love Chicago because I know the market decently well and more importantly have a VERY SOLID TEAM, of people I know, like, and trust!  

I still keep in touch with people I've met a decade ago!

I personally like the buy-and-hold strategy and we help clients who share this long-term, wealth building mindset. 

Trump has said he plans to keep owner occupied rates at 6% through 2026.

Did you keep some coverage in case of major lawsuits? 

i'd pick a market close by, or that you have a personal connection to, or that you visit often.chasing cash flow by itself can lead to negative outcomes - for example, these investors bought in supposed "cash flow" markets:https://www.biggerpockets.com/forums/12/topics/1215726-break...https://www.biggerpockets.com/forums/963/topics/1195280-expe...https://www.biggerpockets.com/forums/48/topics/1137397-balti...hope this helps.

You absolutlely need to be direct to seller or have close, personal relationships with wholesalers and active agents.

I agree that is will be a gamble as to how well it will do.Also, ask the owner if they will entertain partial owner financing to keep from dragging family and friends into this risky business venture.Maybe even rent from owner for a year with right to sublease to see how it goes before committing to a purchase.