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. 

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.

I would be delighted to discuss further and provide information on our current market and available inventory.

What are some unexpected challenges you've faced?

Florida is really competitive with short-term rentals and I've heard many stories of people diving into the market over the past few years only to find it difficult to cash flow with unexpected costs, rising interest and insurance rates, higher price points. 

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. 

These expenses can include property acquisitions, development costs, or unexpected repairs.