For this reason some people prefer to hire a company that just cleans and scopes and doesn't do repairs (the ones who also do repairs may be biased and recommend expensive repairs 100% of the time). 

For illustration purposes, you hire a snow removal company, they are ultimately negligent and don't perform the services they contracted and there is a slip and fall incident.

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?

I would like to hire an assistant as the business is growing.  

You hire people do this.

You can’t swing a hammer you have to hire somebody to swing the hammer.  

Don’t want all of my insurance policies to go up or deal with the hassle due to this neighbors negligence.Worth hiring a lawyer to send a demand letter?

What your goals are for any purchase are very important.You sound like you may have just hired anyone as your agent.

The expense of making an error or hiring the wrong contractor can very quickly be much greater than just hiring a PM. 

When the time comes to evict our first tenant, I will hire the best lawyer and let the expert take care of it.