The current seller is willing to seller finance, but I am concerned about holding it for a year due to negative cash flow and speculating it will still be worth more in a year.

Is it positive or negative?

Also if you do buy your own home, assuming her name would be on title, her debt will negatively impact you.

You don’t want another negative holding you back.

I fix things, do upgrades and do my best to bring new tenants into the building who will follow the rules and not cause disruption to the other tenants.We've all noticed recently the media (in general as well as social media) seems to enjoy giving attention to the bad landlords (mainly the harsh letters some landlords are mailing to tenants) and that certainly isn't productive however the media/social media often tends to enjoy broadcasting negativity. 

I know, I know there maybe some negative connotations for it, but man... how beautiful is our world?

We have no rent or eviction orders in place and we have had no negative feedback for the tenants.

Depending on how I file Property #2 for 2019 taxes, what could be a negative impact if I chose to convert Property #2 to a rental in 2020 and hold for the long-term?

The opportunities will be there, those of us that can weather the storm will be in a position to prosper.Do not get caught up in the negativity of the day, see the opportunity, take the time to better yourself and your positions and be ready to pounce when these opportunities present themselves, this virus is pressing the reset button in a lot of ways you just need to stay positive so you can see the opportunities for what they are when they come! 

Unless vacant lots are selling in that community, some tear downs actually have a negative value. ie, I wouldn't take them if they were offered to me for free.