2) If we work out the details, and proceed without the help of VRBO, should I make him sign a simple month to month lease?

Here are is my advice if yo wanna try outHave a Professional website direct to the point REMEMBER first impression is the last impressionTry to create engaging content and share on your facebook pageUse a Professional profile picture and nice cover imageRun PPE ad and target your the group of people you wanna target, interest, as well as locationLet it run for few days make sure you add your facebook pixels in your website before you run ads that will allow you to track what happening and also add Google analytic to your websiteGet a designer to design nice ad image for you LESS TEXT MORE CREATIVE.Run it for few days and keep tracking the process and after few days start a retargeting ad as well with it so people who visited your website showed some interest and than left retarget them.Above tips were simple and to the point.

If you are looking to strictly buy another place, I would probably take the cash out by just putting a loan on it, but if you're looking to pick up some distressed properties, fix them up and put them on a loan(BRRRR strategy), then I think using a HELOC on that existing property would be smart as you can draw and replace the funds essentially as much as you would like to snowball the portfolio.

I am not sure if I fully understand how to pick the right deal.

Sorry for these seemingly simple questions.

You would be able to pick the best to keep for yourself and wholesale your excess to other investors. 

I am interested in learning about many different types of real estate strategies as I have not picked a specific Path to focus on yet.

Maybe you don't have tenants yet so that is a moot point.My approach in rentals and business is always to just go as simple as possible.

I can't see anyone coming in, loving in, and saying "oh, but I think it's laminate up top, no thanks".. they will pick it based on location, amenities and price!     

Some benefits I have noticed while househacking in my triplex:- I am at the property daily and can stay up on any maintenance and issues without having to remember to drive by or check in with a property manager- Rent collection is as simple as a door knock.- Tenants generally will be less inclined to try any funny business because they know you are right next door (or above/below them)- It's more conducive for learning as you go.- More favorable loan and insurance terms for an owner occupied property.There are also downsides such as:- Less privacy- Blurring of the landlord vs neighbor relationship- Can be harder to be the "bad guy" on things because you see your tenants often.