Several things to consider: 1) One of the main purposes of segmenting your assets into separate LLC's is so that your personal net worth or equity in other business ventures or properties isn't exposed, so unless you have a high net worth or a lot of equity in a property, it might not be worth bothering going the separate LLC route, especially when it restricts your financing of the property.  2) Most any commercial financing you get from a local bank for a small property is going to have recourse anyhow and require that you sign a personal guarantee, so you're still personally on the hook to the bank even in the case of a commercial loan.  3) If you're a newer investor and buying a deal that's tight on cash flow, or if you don't have a ton of cash sitting in the bank already, your greatest risk factor as an investor is your investment failing economically due to poor financing terms or not operating the investment properly, not because you get sued. 

You should have separate LLCs and separate bank accounts for flips and rentals. 

Best first property to buy IMO is a househackIf you have 150k in my market you have lots of room to buy a very nice duplex that is comfortable to live in a really separates you from the other unit

Safely leverage the equity and find a separate investment property. 

I am hoping to find a single family home that I can "BRSTRHHRR" (buy, reno, Short term rent|House Hack, refinance, repeat) by creating a separate living space in a single family home that can be STRed (this is due to local restrictions in my town that prevent STR in multifamily properties). 

If you're not timebound in a deal it could be worth paying these guys separately $250 for their time to walk you through a house and build out an estimate, that way you have an idea how they work for future projects.

I guess i'm looking for software that separates tenants, from PM, from owner well. 

They're close enough together that you'll have trouble separating root balls on each plant.

A standalone ADU is almost always going to cost more than doing an addition, so the value added or cash flow increases will have to justify each.I work with a team of investors who will buy SFR homes then build a new ADU on the lot and add a separate drive way and meters for utilities in North Texas. 

It has been mentioned above but your best bet is to separate the SFR and the 8 unit into two separate transactions.