The price point will be determined by how much time you spend searching for properties (MLS vs Wholesalers and private sellers) and how much work you want to put in to get it cash flowing (level of rehab and sourcing and selecting tenants).

I had a similar situation , I kept the house clean , neat and liveable for 10 years , when the last tenant moved out , full gut down to the studs rehab , everything new . 

I have experienced cash flow anywhere from 10-18% with so much more to offer.

Your entire HELOC would also be tied up in one (or maybe a couple) properties.It's very difficult right now to cash flow positive on BRRRRs at all and so you'd only be less likely to do so with a HELOC.So... won't work / not a good idea

With my current mortgage + HoA at $1600, and my rent at $2700, I have cash flowed around $1100/month since moving out in January of 22.

I will be putting anywhere from 3.5%-5% down on the property so with that in mind, would y'all recommend starting with a Multi Family and reduce my living expense or with the SFH and not cash flow until year 2 when I am out of the property? 

Thanks Scott I got a nice mention this week on Dave Meyers post about RE asset class. and one of the BP members a few years ago sent me a nice e mail and we talked through a deal he was doing and he gave me some credit for helping him structure and or giving him encouragement to go for it.. and I believe he said this year that one deal netted him 143k in cash flow.. talk about a Yatchzee..

It would cash flow as a rental property but not as much as a multi. 

DSCR/ rental loan will go off strictly the cash flow of the property, in this case it would be negative DSCR if the monthly payment is $4600 on $4000 rent. 

You discover his unauthorized dog trashed the carpet in the living room, destroyed a couple doors, and the entire place needs cleaning.