Putting aside the fact that it probably makes more sense to get my start somewhere relatively local to me, I was still wondering, for you fellow Canadians (@Marie Shaug , @Roy N.) who have some experience investing cross-border real estate, are there any resources you could point me towards that would help give me an idea of what kind of additional expenses, taxations, or other considerations I need to take into account if I end up going that route?

Owner says they haven’t had any failures. 1) Is there a warranty or insurance product out there I could get seller to purchase to cover the systems in case they start failing.

I can only tell you my experience; both personal and observed during my 40 plus years successfully investing in property, notes, and real estate related securities.First I suggest education.  

The hoa covers so much that you would typically have to worry about with a home.

If I go buy a house as an investor right now using a rent to own model- there is no way the market rent would cover the nut- investors have had a hell of a time trying to even break even these past couple years.

Additionally there is a $35 desk fee which covers the internet, office etc...Also every month I have to pay my own E&O insurance which is about $25.I wish you good luck in your new business!

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+, zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680, some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.

A lot of homeowners will get scared away and it tends to decrease the value of the home if there's anything foundation related in general.

Many just rent part time to cover their costs.