As far as checking your accountant's technical competence, you can use this old but still applicable questionnaire:https://www.biggerpockets.com/forums/51/topics/792277-how-to...Other questions that you may want to ask are listed in this post:https://www.biggerpockets.com/forums/51/topics/795929-questi...3.

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

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

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.

As an individual investor it’s nearly impossible to wear all three hats and execute efficiently and effectively, especially on a large scale.

I'm excited to join this group of like-minded individuals passionate about real estate investing. 

How are you going to get "top lenders" to compete for your business,, if you haven't even established a relationship with them?

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.

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.

The idea is to convert a multi-family building into condos; but not in the traditional sense where you separate pre-existing apartments into their own condos; but in a way where you combine the common areas of all of the apartments in that whole building, and turn the individual rooms within those apartments into condos themselves; thus transforming the hallways, kitchens, bathrooms, living rooms, dining rooms, porches, balconies into common areas of the condos.