This project won't be a consideration for at least another month, if not more, so I've got time to interview more contractors before I even consider an actual offer on the property.

If you can't find a solid RE investment, then consider an REIT if you are focused on RE diversification.

Therefore, people cannot build up the bank account to even consider an investment property. 

Consider an alternative form of investing such as HML.

The Dunedin Causeway is beautiful, but it pales in comparison to what we locals consider an actual beach.On the other hand, Clearwater Beach just to the south is in high-demand (with the price points to match), but we locals would never go there.

Pulling lists from your county (tax delinquent, probate, evictions) or from the city (code violations) skiptrace the numbers and cold call them asking if they would consider an offer on their property.

Another option is, If you know you have a buyer, and the seller wants a huge EMD consider an option contract instead.  

You may want to consider an umbrella policy to give additional Liability coverage if the limtis on your homeowners are exhaused. 

You might consider an LLC or an S Corp to simplify things, it wont let you split every property differently if you hold them all in one entity but it will make distributions much easier than if you were trying to keep track of each property individually.

Consider an SFH or MFH and a good property manager so you are not dealing with the headaches you mentioned.2) As a new investor/LLC, your company would not be eligible for a traditional mortgage.