Previously, to see if a deal was any good, I just let my financial planner figure it out because I thought it was all too complicated. 

As I said, I have met with financial planners and a CPA.

The loan, OTOH, has no effect on the taxable gain.I would advise you to sit with an accountant or financial planner and go through the number in detail, with consideration of your other income, and discuss future goals.

If you go this route you'll need some pros on your team - a Qualified Intermediary for 1031s, a tax man, and fiduciary financial planner to help with the ins and outs of the trust.

I was kind of caught by surprise and felt like I just keep spending money, of course its was well worth it, but I am a planner so finding out when something is due drives me crazy.  

At that very moment, I knew I made the right decision to create my own site.Plus, their training videos discussed integrating Keyword research (Google Keyword Planner, Uber Suggest, KWFinder.com, etc), creating crediability within the About Us page, remain frequest with blog post, create squeeze pages, etc.Nothing is a secret sauce anymore.

I was told by the district's planner that a residential facility which houses 3-5 Unrelated adults is permitted in all districts except Limited 1 Family.

Call your city's planning department, ask for the planner of the day and pepper them with questions.

Our clients are for life just like your financial planner, dentist, doctor, insurance agent, attorney, etc...

TL;DR: Looking for a financial analyst/planner to help me with quantitative tradeoff analysis to help me decide whether I should sell (some subset of) my 5 rental properties so I can afford to purchase a single family home and stop "throwing away" ~4K/month on rent.