The Hilo side of the Big Island does have the best chance for cashflow positive lower cost properties in Hawaii, but it still takes skill and some hunting (just like anywhere). 

@Dev Horn is my good friend at www.webuyhouses.comDev I know you would agree that the skills of negotiating with home sellers and giving them "cash or terms offers"  is probably the hardest skill to learn 👌

If I cannot - or am unwilling to - meet them, I will bow out of any mentoring I may be offering to do.I'm here to make a difference - not propagate the status quo.

Most people in that rent bracket live paycheck to paycheck and do not have the financial skills to keep a balanced checkbook.

Their subscription fee is about $25 a month or so, or if you are Realtor you get the information for free from them.However with statistics...always keep in mind the old Mark Twain quote...There are lies, there are damned lies, and then there are statistics.Knowing the numbers is a start, but understanding how to properly interpret them is an entirely different skill.

I use loopnet listings to practice my analysis skills on apt deals.

However, I'm wondering if I would be jumping the gun too soon, as I don't have any real estate specific experience on my resume.So, my question is this: Do you think that the legal side can impart any value-add skills that will be transferable to the business side of real estate?

Our skill set will differ from that required to run a rooming house whose clientele are employees of a local institution (i.e. hospital) or industry (i.e. auto plant) which is again different from a rooming house whose clientele are the working poor or on the verge of society.One thing that, we believe, is key in the operation of a rooming house is to have a live-in "Den Mother" / superintendent whom you trust.  

I would like to learn that skill so when I invest and sell, I can do this myself.

I am contemplating going back next fall, but not sure.In the past year I have taught myself coding, so I try everyone in a while to get side work doing that, but without a name or portfolio it is difficult, but I have started creating a Real Estate website that I think would do VERY VERY well with Real Estate and would have the potential to compete with Zillow/Realtor.com , but I do not have the skills to create everything needed, so that thought is on hold, probably for a decent amount of time.Now that I have given my background.