I see a lot of potential in your situation, and I’d love to offer some insights based on my own experience and what I’ve seen work for others in your shoes.A couple of years ago, a freind of mine, also a sole provider for his family, faced a similar dilemma.

Knoxville I would consider a different market demographic entirely and I don't have any insight there.I would caution against taking your realtors word at face value. 

While I own quite a few rental units already, I thought condos might be a good option to gift to my kids when they turn 18, offering them a safe introduction to property ownership without too much risk.However, my challenge with investment condos is that the cash flow always seems terrible.

Quote from @Michael Challenger: I have no qualms with hard money lending, but I need to learn more about the process and structure to these for typical deals so that I am more comfortable and in a position to reduce my personal risk and risk to investors as much as possible.

Get a small MF you can house hack and start that way.I'm not an expert on the auction scene, but, from what I have read, that is a challenging first step into investing. 

The challenge is to figure out:  do you have a distressed syndicator or a good syndicator?

Flipping on a land lease with high HOA fees = challenges that could impact profitability. $700/month HOA fee may deter buyers, elongating your resale timeline, and could push your ARV closer to the lower end of your range.

I do not buy the bi-level house on a busy street facing a factory! 

Challenges?

Hopefully, some of the lenders posting here can address that challenge...