Removing a property from the C Corp, to refi or for whatever reason, would generally be a taxable event.Then you have to contend with the personal holding company (PHC) tax that you probably will have exposure to.Then you have consider double taxation, as @Natalie Kolodij mentioned. 

Currently, my leading contender is installing some sort of metal edging, rolling out ground cloth, and then spreading out a few yards of crushed stone.

In your 280 vs. 310 example a seller or listing agent may not have thought you were a serious contender.

I'd assume you have state/federal foreclosure laws to contend with, right?

Oftentimes, your insurance company contends that you failed to disclose risks during the application process - therefore your claim is rendered invalid based on these allegations.

Kristofor, please do yourself a favor and find a (one) realtor who works with investors to not only find you contender properties but to assist you in completing the property analysis, determining market rent, and rental demand in what is known as the "Greater Tampa Bay Market." 

Some people can't see past "work in process" so we have found that once we get past the "ugly stage," the sign goes up and we start showing and screening contenders.  

Also, have the realtor pull you contender properties now and the market rent they command. 

Buyers often lose sight of the fact that there might be structural problems or defects that they will have to contend with later.To avoid falling into this trap have a good idea of exactly what you should be looking for before entering the home.

Such is the nature of the cycle.I contend that today, more so than at any time in the past 8 years, what really is most important is the quality of the market, sub-market, and the deal.