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.

I’m passionate about real estate and am working towards building my investment portfolio, with a goal of acquiring five rental properties over the next five years.I’m here to connect with like-minded individuals, learn from experienced investors, and share knowledge along the way.

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

Hi BiggerPockets community,excited to connect with like-minded individuals who are passionate about real estate investing.

Additionally, add in the ambiguity/risk of the due on sale clause or ramifications on the conventional loan of transferring the property from your individual name to an LLC - the economics don't make sense, and the headache isn't worth it even if it did, in my opinion!

If a cash out refinance, many lenders will allow the cash out to satisfy the reserves requirement.DSCR lenders generally let you vest either individually or as an LLC.

This is a fine needle to thread because at this size, you very quickly start competing with high net worth individuals who are seeking summer homes. 

Very unlikely unless you find a private lender/individual to do this as a one-off.