They were asking $15k more than we paid for our rental we bought off the MLS. 

Less expenses: Stop going out to eat so much, trade your car for a cheaper one, sell the $5000 golf clubs for $1000 ones, 1 vacation a year instead of 2 or 3 a year because "I deserve it", cut the grass yourself.I am being a little silly, but seriously get on a budget and see what you need to do to cut expenses or where you can work a little harder.

Maybe the "classification" isn't the important piece - but can I write off expenses if I occupy a property more than 14 days?

She pays rent on Zelle through multiple other peoples names, and so I am getting partial payments (though she hasn’t paid the total amount) which I think means I can not evict her.

I would likely try to make at least 1 unit an STR to try and get a bigger return but conservatively I would be increasing my monthly living expenses pretty significantly.

They paid partial, about 60% of rent, on the first and I told them to do what they could to get caught up with the following rent on Feb 1st .

Hi Jeffrey, horrendously expensive for what it is.

Obviously I’m in Canada so would need a property management company so that would add to the expenses, but I don’t know, something feels right about an investment like this.

This is going to affect your purchase price, turnover ratio, maintenance expenses, etc. it also may impact your exit strategy when it’s time to sell the property. 

I just am unclear if he has an allowable right to plow over the area and plant grass on about another 1/2 acre of my property that I will then have to have my yard crew maintain at my expense.