Cold areas have climate controls that aren't as commonly found on our side of the country you may not be familiar with and can be expensive to maintain.....

There is a lot of uncertainty with the climate in which we are operating in.

Im from Florida and in this climate your best bet is figuring out which one of those jobs intrigues you the most and just contacting those local business.

I am not really helping you for your immediate question but I can only suggest moving away form section 8. especially in this climate where the landlords are double enemies. anything to do with the govt is a bad deal. especially now. 

The people dealing with this disorder is unimaginable for me.

Unless you can find some home run deals to wholesale in this current real estate climate, its unlikely you can make a killing in a 3-6 span.

However due to the climate and without sprinkler systems, the lawn naturally deteriorates over the years and I start to get HOA requests to repair it.

With the current rental climate and evictions, landlords have very little ammo to work with.

Now waiting to hear about some climate pandemic.

That is a very similar list to mine when I moved to Chatt in 13' from a colder climate.