I think the biggest challenge is making sure you have systems and operations in place early on.

I would take a 1920s property that has all new systems over a 1980 property that hasn't been touched. 

@Devan Dorzok Any time you buy something with a septic system I highly recommend an independent septic inspector.

One's name is Bob Diamond - America's Tax Sale Attorney and the other is Shawn Buige and his system is called Surplus funds riches. 

What's the condition of major systems like plumbing, electrical, and roofing?

The support system I have set up is Connecticut based in the Hartford County area.

Keep in mind, you will likely have to install a sprinkler system, among making other changes for the home to be used for that purpose.

They need a lot of systems to be in place and need a LOT of attention on the marketing and maintenance sides. 

You can also look at Schedule E, which connects to depreciation, though it won’t show the exact cost basis.Since depreciation affects the final cost basis, you might want to ask your CPA for a summary of your properties' bases to save time in the future.They should have a system where we can give you not just the basis but also a detailed gain (and estimated taxes) calculation within a day.

A couple of considerations that differ would be these off the top of my head:Take a look at the septic system.