Some of my Scottsdale connections who specialize in land deals have been whispering about how a few smaller outfits in Casper.. from what I’ve heard, outfits tucked behind older storefronts, have been matching buyers with off-market parcels that never even hit the usual channels.If you line up your financing carefully (no legal or tax advice here, just speaking from experience), you can sometimes lock in a deal that ages nicely over tthe years.

One of the biggest pitfalls is the age of the buildings I'm looking at. 

It wasn't a good deal $90k because of the age, weird layout, and the bathroom was tiny. 

Aging reports would be another avenue to explore, but again, may not even have these.Lastly, while maybe this property is in a desirable area of town with strong demand from highly qualified tenants, but I get the impression this is a rough part of town, with very limited demand from tenants.

And what is a "mileage book" anyway in the age of navigation apps?

Even though there are multiple variables to assess here, what's the age of the property? 

The other thing to consider is the age and if you add a second floor will the entire structure need to be brought up to code for hurricane and wind.I live in a neighborhood where the homes are older (not in florida) and the foundations are hollow core CMU and adding a second floor would not be feasible due to soil bearing.

I fund land flippers in all these states and at your age I would be hunting down a parcel now U want to eventually move to...

Old age?

When I was his age and even into my early 30's I had a fear of speaking to people or publicly and am comfortable doing it now, but we have felt this is a good skill to have.