You'll know when the time is right, ideally you'll be closing 2-4 deals a month in real estate. 

I'm leaning towards going towards the cheaper side, and ideally want something thats going to build equity well based off location.

I understand my income is not ideal for loans, and I have no credit score at the moment.

So not separate living spaces (like a duplex or triplex).My goal is to probably liquidate the asset at the 2 year mark and invest the no taxed capital gains + downpayment + mortgage principal towards real estate outside of my primary residence so I would ideally like to keep it (from a tax standpoint) as my primary resident vs. doing a 75% rental & 25% primary etc. as the numbers don't work out to keep it long term as a rental.

Best you could do is narrow down the comp situation, then possibly consider a wholetail/wholesale play, and if you do, you make sure you have a contingency in your contract tying up the property that you can get out of the deal with minimal, ideally no, damage

Ideally would like to find a midtown triplex/fourplex near the metro in the $500-800K range where I could add value.  

Ideally, it should have some sort of email capability so it can automatically receive lead information from Zillow, Realtor, your website, etc..Some go so far to give you reminders when you haven't communicated with a lead in a long time and can give you predictive behavior analytics.Obviously, the more functions in the CRM the more you have to pay.

TIC or DST) properties as your 2nd or 3rd choice while you're looking around for your ideal replacement property.

Ideally we will in total put down $40k capital to either buy out right or in addition to a mortgage. 

Coffee farmer is the ideal type of retirement if this can sustain a simple lifestyle.