After a grace period of 1.5 days give another notice and mention legal action or law enforcement5.

Be mindful of a gift tax implications if you sell a house for less than FMV.Also be mindful of transactions between related parties when selling at a loss.

Double check your lease, all the legalities and still check with the landlord....

If HOA by laws state past due owners are responsible for all late fees and legal expenses for collection hire an attorney to go after the past due. 

You could see an attorney or even better talk about it with your financial planner many have legal tech now that makes it essentially frictionless to get your estate work done and keep it updated.  

But I just want to start the conversation so we can negotiate the terms so it's beneficial for both parties.

But the best part is the guy I rented to is going to take the super job (trash, sweeping, snow, minor fixes) so that really like 3000-3100. 

Landlord friendly laws keep you safe(ish) from legal disputes with tenants and there are pockets in both markets that are appreciating at solid or better rates.

I've done a couple of direct loans, but for the most part, I work with a mortgage broker who brings deals to me.

You paid 1% origination, closing, legal etc, and 4.5% interest.