I think a great strategy would be to find someone who would like to house hack with you, and maybe even someone with a bit of experience local to the area that you trust and know very well to go in on the deal with you.  

Also, there really isn't any great advantage to automatic payments from my experience.

It's probably not going to end well for that landlord.

I have around 8k saved up and my goal by the end of the year is to close on my first rental property!

Wait until it's close to the end of his lease (know what the law requires) and then give him notice that you will not renew.

I would have been ok with the latter numbers because I have been stockpiling materials for like two months, but...I did not know if I could trust them due to the lack of "professionalism," and my lack of experience. 

Give them notice that their lease will end and you expect them out by a specific date/time.

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

You don't need to know everything to get started; you need a foundation to build on, and the rest will come through experience and then refining your education.You can build a basic understanding of investing in 3-6 months.

I'd say three months on the short end to six months on the long end.Oh!