One of my concern is the fact that he is sometimes irresponsible and may potentially waste the money you give him. 

Would love to potentially find a lender who is savvy in this exact situation.

What to look out for in determining potential neighborhoods (I am not local to the area and is curious on how "hot" neighborhoods started out and what signs to look out for)How bad can a bad investment be?

I'm aware that 4 months is probably not enough time to signal consistent rental revenue for a potential investor to justify a multiplier, however I still wanted to evaluate the possibility and seeing if I could sell it.  

You got a good thing potentially if you play your cards right imho

It's there you can meet potential business partners, funders, other investors, etc.

One concern I have is the tenant turn over process and how best to handle the inspection (security deposit), cleaning, keys management, and potential showings for new tenants.

We can generally do a turnover within 24 hours (sometimes with a punch list of remaining items) but this time around we are getting a lot of interest from potential Section 8 tenants. 

That way you would gain experience, be able to siphon off a portion of that person's good reputation when you are trying to attract investors yourself, and you will make money in the process rather than potentially losing it.Most successful syndicators are looking to systemitize their businesses, and would like to hire someone at a low cost to do the work they don't enjoy doing. 

First thing I look at is the very strong potential that I'll have to replace that tenant.