The second was to get a 1/2 handheld exploratory scope camera.

Number one, I would say consult some tax and estate professionals, as this is a bit outside my realm.If do go about buying it and then rehabbing it, make sure that you have a contractor walk the property with you (shouldn't be a problem since its family) and figure out what your scope of work is.

Are you the GC in these builds or did you contract out that scope?

That's out of my scope for now.

I looked at the data on FF when I scoped out my area as well.

If you provide a detailed scope of work to your accountant, he/she will be able to properly identify what is a repair / improvement.If it is an improvement, he will want to see if any amount can be immediatley expensed through the de minimis safe harbor election.Best of luck

This is because there's less square footage to renovate, so the project will be smaller in scope (and cost).

An additional great recourse for legal questions not within the scope of this website is avvo.com where lawyers join and give general legal opinion on topics posed just like on biggerpockets. 

My reasoning is - buying two homes in the scope of several years will have additional closing costs you might not be thinking about as a new buyer (you will essentially pay around 8-10K each time you buy a home).

What is the scope of the work you are doing here?"...