I’ve been documenting multiple comps close to my house tracking rents and it seems like my house would rent around $2,000/month.

By the time you need to evict due to hoarding they have probably violated multiple other more definable lease clauses.  

So you're absolutely right from a PMS capability that some of the major players include Hospitable, Guesty, Lodgify, Ownerrez, etc. 

. - I've had multiple vacancies, including one where the tenant left after a year and cost me $6k in turn costs.

In the last 2 years we have had two different properties where tenants left a bad flea problem behind, and it's a PITA to get them gone because you have to spray multiple times and vacuum everywhere multiple times. 

For schools, Omaha has an excellent public school system and has multiple counties with nationally ranked high-schools.

Deal makers- development potential, vehicles per day, road ingress egress off highway, signage potential, multiple road accesses, value add potential- housing- trees, boulders, ponds, walkout, views, right side of town, power-line right of ways, etc6.

Not sure the rules in NY real estate, but it's best practice to interview multiple brokers and understand what you are getting yourself into beforehand. 

I use Regus for multiple businesses.

Buy good quality things once rather than poor quality and pay multiple times to replace it.