I'm hoping to connect with established investors in Chicago and would love to help you in exchange for some wisdom.If you're interested in meeting for coffee/lunch in the city next week please reply or send me a message.Best,Bret

I am 7 months out from discharge and preparing to re-establish bmyself and make up for lost time through teal estate investment.

Or do I establish some relationships with hard money lenders first?

@Josh Magnus I would suggest to proceed with caution...but proceed nonetheless...In the area where I focus most of my attention, 80% of the houses for sale are places that were sold last time in 2006-2007...Most of them investors who finally manage to match the price they paid for...As most commentators said condition now are very different then 2008...but that doesn't mean crisis have to come from the same direction/cause to get the whole economy crashing along...Brexit...trade wars...student/consumer/corporate debt...there can be many reason for the next fall...and in 2008 nine out of ten economists didn't see it coming...that will probably be the only constant.As someone who also work full time my suggestion is to narrow your focus on a specific area like 1 zip code and follow it to exhaustion...know every house that get to market...walk the street with google view over lunch break...analyze city/county records for every property that hit the market...check all rentals you can find...establish working relationship with one or two buyer agents...this way when something arrive to market you'll be in a position to act fast enough...I got one house that way and now in contract for another...both were sold last in 2007 and on both I offered asking price (=2007) the day after they got to market...if the numbers work for cash flow then the state of the economy is much less important...and be picky (don't feel bad passing on houses)...personally my goal is to be able to become at least part-time when the crash will come so I have more time for RE then...good luck!

Now that we have established that this deal is over my head, I have a follow up question: how do I make the most of my time with the agent tomorrow?

There is tons of opportunity in the $300-800K range and doing a couple smaller deals will allow you to establish a track record which ill attract the bigger money down the road. 

We used some HELOC funds to replace windows and the roof on our primary residence and now owe 30K.I would like to use the house to help establish the LLC and am looking at two approaches: 1) start the LLC, apply for a BLOC, use BLOC funds to purchase the house for the LLC, or 2) refinance the house and use the funds to pay off the HELOC, establish the LLC, and provide an initial operational reserve.

Not sure what point you are establishing.  

However, buying in this way without having an association established creates a few lending issues...They can be overcome, but have more hassle and $ attached to them.

Those on fixed income may not be amenable to any future rent increases, so it can become a problem if they want to stay long term in an area with increasing rents, but may be welcome in established area where you just want longer-term stability.