Get your bearings in the rental business 1st then move into that down the line.

They back dig it, put in gravel and drainage, pull it plumb and tie it into the back soil.

Before buying land, I would make sure to hire the right experts to assess the land topography, it’s soil quality to determine what size septic would be allowed.

.)#2 Rezoning to Approved Plot Plan where you hire engineers to get plan approved by the city/town to have structures built on the land#3 bring utilities to the lot line ready to go (water, sewer, gas, electricity) if out of city you may have to build your own waste water plant or septic system for sewer and drill well for water#4 clearing trees, grading land to have soil elevation to be relatively flat#5 bringing all utilities to each individual lot (residential subdivision, mobile home park) #6 build roads Hypothetically speaking your $100k raw land could be worth $250k after its been approved by the town to have 10-15 mobile homes built on it or worth $350k after you cleared all the trees and grading and have all utilities at the lot line.. 

I'll provide my two cents on your questions above--please bear in mind this is a complex topic, and there are no black and white responses.

My family has always traveled to Big Bear, CA at least once a year for New Years, and I loved the idea of owning a family cabin that we could stay in for years to come.

Recessions and how strong they will be are notoriously hard to predict, but if a significant one occurred in the time period you've listed, that changes a lot...

Also, bear in mind, that our downtown is tiny. 

I ask because I am looking at purchasing property in Chester county as well and am trying to get a stronger bearing on what areas to avoid etc.

I have one that I inherited on a property (in a ridiculously safe area, no less) and it's pretty solid and would be a bear to steal the unit.3.