Outside of potentially costly trial and error is there a good way to learn about the necessary forms and contracts so that I'll feel comfortable with this area of REI? 

Shop around and be sure to take advantage of any free trials so get a feel for the software.

They waste their money they would have been better off saving for a deal because they want the real estate equivalent of a diet pill.

They offer a trial for 10 days.Two landlords friends of mine use Appfolio and TrueRent.They have 60 & 25 tenants respectively.

I understand the trials and tribulations of working with friends and family, but I am willing to take these on for my first deal.My experience in real estate isn't super extensive but I am a data engineer for my day job with a background in statistics and finance.

The truth is, you could read 100 books and still not know enough because certain things need to be learned through trial-and-error.

So, I would give  him a trial run.

After starting this thread, reading everyones helpful advice, and suffering through a little more trial and error, I think I have finally solved (at least for now) the riddle of successful posting on Craigslist.Since tweaking my methods and figuring out what I was doing wrong, all of my marketing ads are posting and "sticking" with no problems.

Less than that really, because my Google works free trial is 30 days. 

If you're keen to listen to books, you could "read" it for free by doing a free trial with Audible.com.