Why would an investor deliberately swim up stream?

I'm deliberating whether I should hire my neighbor (he just had leg surgery and walking with a cane) across the street to do construction because if the construction turns out bad, I strain the relationship with the neighbor across the street, and also whether I should hire my neighbor from another place who does the design because I kinda don't prefer he knows where I live (just because if the design turns out bad, I strain another relationship with him and exposes my address of where I live).

You won't really find "deals" on the MLS unless you find a motivated owner that has deliberately priced their property to sell fast.Otherwise, you look at properties on the market for 90+ days and make offers at an amount that makes your ROI work:)Yes, you may have to write 10, 20 or more offers, but write enough and someone will eventually say yes. 

I'd also add when talking to their landlord to make a deliberate error with the house number or street name. 

the reason any and all parties that could be named in a lawsuit are named from the beginning is because in the discovery process of litigation, it may be uncovered that you (personally) are liable (through piercing your corporate veil or other deliberate acts) and that suing attorney can have additional recourses (EG your personal assets) to go after. 

There are times in most people's lives when renting makes sense, and I don't think any more or less of people who rent one way or the other - but lifetime renters who haven't deliberately chosen that path are generally there because they blew opportunities everywhere to own their own home, and if it doesn't bother them to be renters why should it bother me to charge them rent?

Once in awhile, some internal person makes a mistake and there is a slight delay.The bigger problem is screening S8 tenants to get one that pays THEIR part of the rent on time and takes decent care of the property.We just had eviction court today with a tenant not paying their rent portion AND deliberately causing damages, so their home failed the S8 inspection.

Personally I dislike HOA's, scale deliberately and dont overleverage.

My next move needs to be an apartment bldg ...and your path all seems very deliberate and tenacious. 

A goal to work backwards from to today so you can make a specific plan and take deliberate action daily towards YOUR goal.