I’ve thought about RE agent, or trying to find an entry level job in mortgage lending, or even workIng for someone doing rehabs and/or buy & hold would be awesome as this is what I aim to do as an investor myself.

You will need some level of training before diving in, and it usually takes a few months of preparing before you are ready to actually buy something.

I heard one of my investor buddies say he's got a municipal tax lien reduced often in our county but you know you can't always trust what people say. 

This creates two challenges for me:1) I'd like to do moderate to significant renovations on the units, and my business partner plans on owner-occupying one of the units, so we would need to permanently vacate one or, depending on the property, even all of the units. 2) In order to make the numbers work I'd need to dramatically increase rents (by several hundred dollars/month) to bring them up to market levels. 

Just get it rezoned and level the house to your hearts desire.

I've been doing some research comparing the local markets looking at things like unemployment, rent rates, income levels, property taxes, etc.

The condo is titled to our family trust, and there is no mortgage, We have been renting it to her for an attractive rent - clearly below market value.2.)

If you are wanting to get some very high level numbers the MoDOT bid prices at the link below are a good place to start. http://www.modot.org/eBidLettingPublicWeb/viewStre...

I also trust on peoples word, but have found that the real issue is not their desire to complete the work but their inability to budget and manage cash flow. 

Please correct me if im wrongdown-payment: 400koriginal note pay off 250kRTF 8kcapital gains tax aprox 20% of 100k (400k-300k)gain ) = 20klawyer and fees 12kNet cash on closing 110k6% Trust Deed for 450k over 15 years will generate about 4k / month trust deed re-occurring expense or initial expense. is there one?