The best strategy for you will really come down to your individual risk comfort level.Whatever path you go with, though, treat the businesses religiously . . . attend to them in every way as separate businesses if they are separate and you'll hopefully uphold the purpose of an LLC with operating as a business in earnest.

If you are renting it out like a rooming house where the tenants don't know each other then yes, separate leases.

A) investors pay less than owner occupantsB) anyone buying a quantity of something wants to pay less than the “each price”In this market I would simply list each separately with the standard “this is part of a 1031 exchange and buyer will help coordinate the sale lingo” Any that aren’t under contract in less than 20 days are overpriced or badly marketed.

Happy to pay reasonable rates, which would be discussed separately.

@Jack Calhoun There are a few "rules of thumb" but ultimately, you'll need to do a full underwriting on a property before you actually put in an offer.I would suggest finding a good property analyzer spreadsheet and getting enough practice that you can quickly do an initial analysis within 30 mins or so.Some things to look for in a property analyzer: Allow for separate entry and exit cap-rateMin 5 year forecastinput for rent/expense growth on each yearincludes rehab and capex costsincludes debt service and financing costsincludes acquisition and disposition costsProvided IRR for planned exitHonestly, there's a ton more bells and whistles you could add, but I would consider that the baseline if you're talking about deals that size.Hope that helps!

@Brian TietjeTwo separate but related issues here.

Should be a nice double on the equity with cashflow along the way, buying it at a 4.9% cap.Debt is going to be 3-year interest only at 3.5% with 2 separate 1-year options to extend.

Instead, locate a SFH with a separate income sweet/ ADU/ Mother-in-law unit already built in the property.

If i may, let me expand / detail some of your thoughts with my perspective.There should a separation between a "real estate business" and "real estate investment." 

I suppose if you are that good in sales and have a market to get $1mil transactions, sure...You have to separate truth from reality...