Real estate investment is always a matter of perspective and strategy, and the current market environment is no exception.

But it feels like if you keep cashing out equity on your properties to buy another, you end up with multiple properties but with your equity stretched really thin, like a house of cards ready to collapse. 

But having multiple banks working the deal I had one pull through for me.

With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

When you go to sell, Montvale requires a certificate of occupancy so this issue has to be resolved in advance of a sale.Although I am not a lender, I assume you will not be approved for an owner-occupied mortgage on 5-units if it is a legal 4-unit without some type of mortgage fraud whether in reported rents, units, or another legal document or representation (very very large issue from a legal perspective with multiple arrests in the last year for anyone playing fast and loose).As far as the DCA, I would recommend coordinating your work with the city with the DCA.

I even offered to let the seller out of the deal, multiple times, but he wanted to press on and just get it done.

It keeps things professional while giving you room to grow your expertise.I admire your perspective on keeping your parents’ resources separate from your own—it’s smart to want to succeed on your own terms.

It's much easier to set things up right than to have to transition them later when you have multiple properties and many, many transactions.

Have multiple strategies when you're putting deals together so that if one doesn't work well, you can pivot.  

Could you end up finding one or even multiple deals at auction?