Your best bet is to get a couple contractors/handymen to look at it and price it out because without all the specifics price is just pure guessing.

Once you do that for a few years you can move out and repeat the process or start buying pure rental properties.

Then after the repairs and rent increases, you can basically do a BRRR paying off your heloc and you now have your home and a 8 to 12 unit apartment that is pure cashflow.  

In the past if you are moving to a single member LLC purely for liability protection most banks will not have an issue with it.

How, or why, should it be any different with purely private sector mortgages, since these are a legacy of the insurance industry?

We are purely online retail so would like to avoid payroll if I can.

Of which both sides will be renovated and ready for tenants in the next few months.We're ready for our next property and would like to do one more hack before buying pure investment from the onset.I don't want to kill our cash cow, but I can't ignore the fact that selling at a peak could put us in a position to grow our cash cow heard.What are your thoughts?

I personally would take the additional income and suck-it up in the smaller space (which is purely theoretical since I'm expecting my 4th kid and neither of these scenarios would have enough space for my situation:) )   Looking for your opinions, thanks!

Duplex’s seem to be getting tougher to make sense financially as a pure investment property IMO unless you’re putting a large down payment into it.

My current goal is to generate enough cashflow through MFP to be able to  "retire" by the time I am 30, and am looking for a job purely so I can fund deals.