Everything has been nicely redone, we only found one electrical outlet that didn’t work compared to the usual $15,000 worth of electrical I have done to most of my buildings.

One issue of doing it within 401k, is what happens if you spend all your money from there, and then have unexpected expenses or lower ROI than expected. 

Show up unexpectedly and let them earn your trust don't just give it out right away.

I did have a family emergency that took me out of office unexpectedly, and caused me to lack follow up for a couple weeks. 

You can go in and offer the county practically nothing for it, but it means more tax revenue for them, and no one would ever build a house or outlet store there.

From what I've gathered the properties will not begin to cash flow significantly better, you are in a market that cannot easily absorb unexpected capital expenditures (greater risk to you in the future) and the principal paydown is pretty meaningless for a while.

. $30k can turn into $8k or 0 really fast - whether that is due to unexpected costs - especially on an 1875 vintage home - or your ARV estimate being off.

What are some unexpected challenges you've faced?

Even a media outlet like The Wall Street Journal to keep up with market trends and other macro factors affecting real estate.

It's going to be a steep learning curve: there are always budget and timeline overruns, unexpected costs, etc. and that hard money loan will kill you every time.