Knowing that I'll have only two properties that have any rental income, I know that I can show my income on a schedule e and that I can claim depreciation on that form.

He has a full time job and is not looking for any office support, leads, or training.

You're best bet is to check meetup.com to see whats being scheduled.

That way, if you take an old window out and discover it's a bigger job than you thought, and you need to go for more parts, you can temporarily board up the opening while you go to the store.You should also use some kind of insulation between the replacement window and the rough opening when you install it. 

I've worked in various jobs over the past 4 years with sporadic flows of income from each. 

Hey @Zasha SmithGood job saving up $140k!

Besides my full time job as an Electrical Engineer I want to build a long time portfolio for financial freedom and satisfying my entrepreneurial soul.

Current situation: Early 30s, both live and work in town in professional jobs (CPA, real estate appraiser).

Good thing you have a good job.

I have recently witnessed some people around me that I look up to have financial troubles in fields/jobs that should be “secure.”