I was a SWO for 8 years, and the best thing I did to improve my financial life was real estate investing. 

Your best rule of thumb for where you are at in life is to not buy anything you wouldn't live in yourself.

If you'll be there for the life of the loan, no worries...It'll just reduce your overhead and will be always favorable.In regards to the syndications and STR's, the syndication would be the 2nd place option.

Its a lot of money to put into someone who's new to their life or the industry.

Even if the sponsor lacking knowledge and experience can raise capital through syndication, their life will become a living nightmare of lawsuits, hostile social media posts, public ridicule, accusations, legal threats.  

I’d look into the cost of a 500 sq. ft. garage and compare it to the potential boost in sale price.

Ok, now, conversely with real estate, that is simply not possible. '08' was the biggest hit to real estate in our life times, of EVERYONE alive at the time of it, right.

I am fairly new to the wholesaler life.

Getting greedy tends to cause investors to be sloppy and I 100% agree with @Ken M. no good deed goes unpunished in all areas of life. 

We got top dollar and set her up with a solid financial advisor to live her best life after loosing a loved one.