I’ve been in the real estate business for almost three years now and have completed five deals: one buy-and-hold long-term rental, one short-term rental, and three fix-and-flip projects, for which I helped raise capital.

Only 100k for all your work barely sounds worth it, with all respect. 

It's on a Main Street (Perry BLVD), and it is on a bus line.About 8 months ago, one unit went vacant, and we can't find another tenant no matter what we try or how low we go with the posted rent.

If I were to invest into one that was grandfathered in, would I have to convert it to a MTR?

I've called a couple title companies there and they are not familiar with the process and one said that the practice CANNOT be done in the state of IL.

All the best!

I'd also start the marketing process 30-45 days before current tenants move out in most cases - it just seems easier to re-let a place that is currenlty occupied than one that's been sitting empty for a while for some reason. 

Decided to grab another one there since we've already built out a great team and the lift to get it running will be light. 

It also appears Investor's Edge may have rebranded from their old company name "Do Hard Money".Propstream screenshot:"Investor's Edge/Dohardmoney" screenshot: if its a reboot of Do Hard Money one would want to read all the threads on that Utah based company.

So anyway one can pay the  20k and get some basic theoretical knowledge but one should be realistic this is a big cash up front business.. your not going to find consultants doing this work on the come.