Do I need to invest in desert properties like I see so many do or can I work the same system ( a few hundred to thousand for small 1-5 acre parcels) in areas like Central MN and Northern WI within lake country? 

And your generally dealing with a home that is 20 years old or less.. stucco  tile roof  newer components etc no freeze thaw issues.. easy desert landscaping. 

Option #2: go out further and flip or buy/hold in the desert.

I spend my year in a few climbing areas. the forests of Eastern Kentucky, the Western Slope of Colorado. and the desert of Western Texas.

., those that are not plots of land in the desert covered in snakes and weeks) going for near market prices?

Especially in those areas...the desert is always the first to crash and the last to appreciate.

I know the Inland Empire and even the desert areas like Victorville would be easier to buy in, but they just aren’t the most idle locations when considering my job.I like your idea of getting into an area that is in the beginning stages of gentrification (Long Beach, Inglewood, etc.) and putting in some sweat equity.

I mean who the heck would want to live in the desert, right?

We have golfing, resorts, river tubing, etc & snow skiing, (half the state is desert valley (Phoenix ) and the other half is mountains (Flagstaff).

Sellers in this market are easy to find.If I was a chainsaw salesmen in a desert i wouldn't be successful because despite having tons of chainsaws, no one needs one in a desert.