For both of these houses, do I need to reach out to each and every vendor with a W-9 and a 1099?

Quote from @Mitchell Gunlock: Investing feels overwhelming, and I get stuck in analysis paralysis.

I am not going to rent a nice house to four 19-year-olds working at McDonalds because it's absolutely foolish, but I will put two of them in an apartment and give them a chance to earn a reputation.

@Shaylynn O'LearyundefinedIt could still be a good investment.

Love or hate DR he exposes the reality of being a real estate speculator he was a house flipper who bought foreclosures. 

Do you already have your first house hack or are you looking to get into your first one?

I bought a house-hack last summer in which the sellers made significant improvement to the property.

You usually need to lock up the deal and get a lot of those things done during the process.Buying near your son's college would be a great idea if you plan on having him house hack there and manage or learn or use one unit as short-term or mid-term for when you visit. 

I am currently in CA and have an investment property in OH.