They are retired without much savings. 

What I’m really intrigued on doing is getting a short term rental, mainly because of long term appreciation and I can depreciate the first year and potentially reduce my other businesses income so there would be a tax savings there on top of some monthly income coming in.

Thoughts I have lately that seem tough to find info on:1) asking owner financing to “subordinate their equity” to me, to utilize all land equity 

Hey Sarah, thanks for the info! 

Definitely can be overwhelming with the amount of info thrown at you.

With the right lender, it only takes a couple weeks.Here’s the link for more info: https://www.va.gov/housing-assistance/home-loans/loan-types/...Your current lender may offer this, but check around.I used the VA IRRRL in 2018.I wish you all the best.

If your intent is to keep this a two unit I would separate the utilities it will likely save you money and aggravation in the future.

I have saved up a decent sum, and now want to get into Commercial Real Estate investing.

Many, many people on podcasts only have a few years of experience (not all, but like @Jaron Walling notes, you can save yourself a lot of time if you skip over the people on podcasts that have only been investing the last 5 yrs or less).  

In that case, use the the HELOC and savings to start investing.The problem I see with selling, especially with the intent to invest, is that there are not a lot of great deals between current prices, rates, and low inventory.