However, because I plan to retire and live off passive income within the next 5 years (age 33), I don't like the idea of money sitting in retirement accounts gaining returns that are inferior to what I could get if invested in buy and hold real estate while not being accessible until ~ age 60.

I think a lot of posters think they'll gain more traction if they use the forums instead, but honestly it's just the opposite - the forums are so incredibly busy that only a few threads manage to stay at the top of the feed.

I was thinking the same.Without knowing all the details, and assuming you own your primary residence...I'd consider selling it (you'll pay no taxes on the gains) and then buy a house that you can hack. 

.#1: There Are ALWAYS People Who Want to Defer Capital Gains TaxOne of the main motivators for many Sellers who end up doing Seller Financing is the deferral of capital gains taxes.

I decided to keep the property because once I decided that I would not be able to take the net gains from the sale and invest into anything with comparable returns. 

And this is you gaining experience!

As I said in the beginning, I am only looking to gain an understanding of what numbers do make sense.

Additionally, it could be worthwhile to invest passively into a syndication in order to gain experience and insight as well as hopefully enjoy returns.

If you can get a better return on new investments (after capital gains taxes) then sell and reinvest.

Patel Gaines Law Firm