My personal preference for a buy and hold would be an already established area (or an area that's still gentrifying, but has already seen significant progress). 

A new person moves in and she says the upstairs neighbors are creating a ton of noise.

The vast majority of contractors won't want to give bids on properties while under contract unless they have a relationship with that person from prior jobs.

Managing five rentals can eat up a ton of time in any given week, often at times that are inconvenient to you and your personal interests (family, hobbies, travel, etc.).Of course you can manage on your own.

The question is, what is the intention  of the owner, not what would a reasonable person think is the intention of the owner.

My recommendation would be to engage an investment property focused realtor (not a general residential realtor) and let that person guide you through the process from pre-qualification to market/property valuation and selection. 

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

I have no idea who I should reach out to for help, and I just do not understand how this person no longer responds to emails or returns phone calls.I hope someone can provide some guidance. 

I mean I got financially wiped out personally..

I don't have any brand preferences personally (I use Fantasy Spas at most of my units but I'm sure there are alot of reputable options), but just make sure wherever you place it is built to handle that type of weight.