Sounds like you're doing all the right things to position yourself for your first purchase.I couldn't agree more with @David Cruice - I think it will be important for you to find a local bank / credit union to build a relationship. 

At this point, however, the cost of entry is very high, and I don;t know if appreciation will continue at the same rateIndiana is cash flow positive immediately, but doesn't appreciate in the long term as much- historically. 

If I won’t have a positive cash flow each month, is it a smart investment?

I appreciate the feedback though thanks!

I plan on using the HELOC/Refinance money to put down payments (or cash purchase) on a couple of more properties, so I was leaning more towards the Refinance because of the rate increase risk, but I definitely see the positives with the HELOC!!

@Walter Aaron Poling Thank you for your feed back I'm definitely going to take your advice and interview a few more agents to discuss my options further and from there.

If so, do you have feedback of whether it's worth it?

The firm I work at has never actually been put in the position of having to uphold the DST's validity, as it is pretty well-established.

There are positive aspects to Wilmington, appreciation isn't one of them.

You are correct, I am squeaking by but still cash flow positive, I take into consideration the tax write off since my 9-5 job pays me $160k a year and Uncle Sam loves me.