At what point it would've been ideal to reach out to the owner to discuss an offer to prevent foreclosure?

Yes umbrella covers what your primary insurances will not; home, auto,  dwelling fire..etc. 

lol3) On the 'detailed targeting' you can just type 'homeowner' and other keywords, and it will auto populate with different options. 

Thanks in advance :)Edit: In case it matters, I'd be focusing on properties in Minnesota, ideally in the Twin Cities area for buy & hold

Obviously, that would be ideal and I will continue to check the market, but would you still suggest that if I could only buy a SFH?

Ideally, the next tenant will also want to stay for a long time, but if you have a shorter tenancy you can show the nice pics and list it and get a head start on filling future vacancies.

The ideal situation would be i go out and find the deals through direct mail, yellow letters, ect.

Auto correct 

Figuring out what our ideal life to maximize happiness was HUGE.

I'm going to venture a guess that your CPA doesn't do a whole lot of returns with rental property on them.The ideal scenario is to have positive cash flow, but a tax loss, but that's not always best for every person, particularly those who don't want higher leverage on their rental properties.Generally, a property that is owned outright or is in the last third of it's mortgage life will show pretty strong profits, even after depreciation.