Ideally, you'd locate a property in one of these neighborhoods for a discount to maximize ROI.Average 2 bed rents for: Bridgeport/Armour Square $1200Logan Square $1500Avondale $1400Humboldt Park $1100Pilsen $1400My suggestion is narrow down and crunch numbers for your cash on cash return goals, cash flow per door, expenses, purchase/rehab budget.

Needs: at least one 3 bed unit, 2 parking spotsCosmetics/minor repairs OK. 

The "real cost " is from 8.5K to 15K depending on who you choose . 

Theoretically, could we choose to close on the first house with a 5% down conventional loan instead of FHA and rent it out from the get-go as an investment property, then still purchase the second house with the FHA 203K loan if we want to live in that one instead?

Specifically, what are investors looking for in choosing a real estate agent?

(Will leave my opinion of that fund for another time) If that is tax free or tax deferred would come into play too.Well, that's an option some people choose because it's quite safe as long as Oregon funds the pension system. 

(in case I later choose to BRRR or househack in LA)? 

We also stayed away from 2 bed homes- only 3x1/2 with garages.

Do not rent to him, hire him as a contractor if you choose.

Choose the ethical route.