I appreciate it.Aside from the option to be added as 'additional insured' they have the option to purchase a  "ProtectionPlus Bundle' from Surevestor, which includes several things like protection against eviction costs, wilful damage to property, over a $1 Million third party liability protection, loss of rent protection for 25 weeks etc.This is $50/month.

But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

I used the lower of rent amounts for analysis. https://www.biggerpockets.com/analysis/rentals/ee5f6928-93ce... is link to the BP Calculation on it.

You'll likely see diminishing returns after 3 bedrooms unless you rent out individual rooms.

Debt will get paid down, rents historically will go up, and values historically will appreciate. 

I believe that's the reason motels rent on a weekly basis.

Outcome currently is a rented basement for $1,350 a month + $130 in utilities while I live in the upstairs unit.

This means that your permanent residence is excluded (except if you are doing a house hack in which the part that is rented out is eligible for cost segregation).

Rent out in the busy season.  

There are a lot of markets with solid job markets, strong populations, solid rent growth, but when you are talking ONE property, unless you are considering highly rural areas, it likely doesn't matter.