Consistent with the advice of @Jo Bradley , if I could get through the first couple years financially, keeping current home seems a lot easier than long distance investing...and at least I know what is wrong with my current home (I.e it will eventually need new roof etc). 

Roof Maintenance/Repair: Done as needed, paid by the owner.

I don't think it will be as simple as trying to just undo what the last owner did; you're going to need legal descriptions of each lot and that generally requires a survey. 

But larger repair items such as appliances and mechanical, plumbing, electrical, roof windows doors etc should still fall under the landlord's responsibility.

Roof ~20 years, STR kitchen 15 years, HVAC 15 years, etc.

Roof cut off?

@Valentina Manzati Because financing an investment purchase is going to require at least 15% down, you're going to need to focus on a property that you can call your primary residence, meaning a 1-4 unit home you live in while renting out some of it, or a 1-4 unit home you live in for a year and then convert it to a rental.

Great property, perfect setup for a duplex with separate driveways, entrances, back patios w/ storage, brand new roof, plumbing, newer HVAC, appliances, flooring, etc.

They provide essentially all the tools under one roof for you. 

The $1300 does not seem out of line at all to me, insurance right now is going through the roof and what would have been ludicrous last year is now looking like the new normal.