Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

You should get some more estimates, but what you are really trying to do is to find someone who has a license and insurance to do it for the cheapest price and that will set off a chain of events that will never end.It's more likely that you bought the house with a wrong scope of work done because you don't have a GC and thought you could DIY it.

You're looking at this from the wrong angle.

What you "have found out" is wrong, at least when it comes to taxation.

I may be wrong but I don't think REIT scales as you are tying up your capital right ?

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.

How AirDNA and others get the data so wrong I can’t say for sure, but I suspect it’s because they can only assume that unavailable days equal booked nights versus any number of different, non-revenue reasons, such as owners’ personal usage, repairs, etc. 

The ones I walked away from I found sold for less but had issues I didn't want to deal with to major issues that I'm glad I didn't deal with.I don't think there is anything wrong with lower-end properties as a jump start - it's just not for me because of the amount of time and effort and tenant base that seems to be a headache.

I could be wrong though...I've been billed $26/month so far. 

I don't think your planner was trying to steer you wrong but it's tough to empathize if you've never experienced owning a family business/real estate.