This duplex will most simulate TWO INDIVIDUAL HOUSES.  

Most (not all) HELOCs require that the property is titled to an individual (not LLC) and are full doc, meaning your employment history, income, DTI etc will be factors.

If you take the individual investor model, you need to find a Whale.  

There are more complicated strategies to maximize larger listings that involve having like multiple listings for same property and do individual room rentals when it is slower and then for larger length stays, larger groups, and more desirable dates you'd book the whole space, but I think its easier to just do two separate. 

We currently accept rent from tenants using a variety of 3rd party apps-Cashapp, Venmo, Zelle but are moving away from accepting payments in our individual names and want to start accepting payments directly to the LLC/business accounts, but LLC accounts do not accept Zelle and there is a fee for using business accounts on Venmo.

As a result, this isn’t the kind of market that attracts top-tier PM talent.Your best solution might be to either:1.Take on self-management if possible (and if you’re willing to put in the time/effort).2.Find an individual you can trust to handle these properties, set up very specific instructions and processes, micro-manage them initially to ensure standards are met, and compensate them well to make it worth their while.This approach requires more oversight on your part but can yield better results in markets like this.

I'm currently building up capital for future ventures and properties that I find on market, as well as attempting to find the best brokerage where I can work under an individual who is already more established.

Use caution when borrowing against your stock portfolio, especially if it's a high volatility portfolio comprised of individual companies.

RISKSPrivate Letter Rulings There are three (3) Private Letter Rulings (“PLRs”) that address this 1031 Exchange structure, which are as follows: Private Letter Ruling Number 2014-08019Private Letter Ruling Number 2003-29021Private Letter Ruling Number 2002-51008PLRs can only be relied upon by the individual taxpayers that requested the PLRs.

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save?