Unless there is money changing hands that lease is only going to cause issues for a landlord.

Do the same there and see if you find any common brokers who list a handful of the size property you want and connect with them. 

So, you are simply suggesting get my, “hands dirty,” with Long term rentals, rinsing and repeating the “house hacking” strategy before even considering STR’s and meeting REPS and Material Participation requirements to maximize tax write-offs on my future W-2, correct?

Then I usually update the financials I keep on hand to align with it accordingly.I'm a CPA but I don't even file my own taxes so please take my response with a grain of salt. 

It's kind of like having car insurance, you don't think about it till the accident but it is better to think about it before hand and be covered if things go poorly.

I do believe hands on is a must for c class neighborhoods.

On the other hand, I would like to hear some recommendations on sites to manage the different postings on different platforms, again I am a beginner with only one villa, so I would like to stay on the $20-$40 a month. 

Treating this child like we treat everyone, as we hand the document to sign: "And this is the no smoking addendum, just be aware, dont allow anyone on the property to smoke here, inside or outside, its impossible to get the smell out of the house" How would you approach this?

Since my father passed away unexpectedly, i do not have cash in hand for the deposit.

Conversely, someone with a smaller portfolio might have a WIDE variety of experiences and expertise in a lot of areas because they are hands-on in all aspects of investing and could give you guidance you can employ in ways that suit you best.