The big question is this - is this 'marginal' area going to a) stay where it is? 

Each was paying me more than $18K for their stay so it sounds reasonable that they would want to confirm it is real and I didn't mind.  

Keep the lines of communication open, and don't hesitate to stay on top of the progress (and costs) as things move forward.It sounds like you’re in some great areas!

I'd politely tell her that if she isn't happy there (which seems to be the case) you will give her the one time option of breaking her lease without penalty if she moves out within 30 days (eg Nov 15) and that she has until Oct 15 to decide if she will be staying or not.I agree with Kevin about phoning and then follow up with a brief summary of what you talked about via text.A lot of people here own a few places (not dozens) and most of us also have full time day jobs, so balance the two. 

Stay in your lane.   

(Existing tenants intend to stay on.)

., you want to stay away from those. 

From helping a widowed mother get a fresh start for her and her kids, to the MILLIONS of dollars in assistance we acquired for residents to stay current during covid...

From now to April has been a slower season for us in that our properties stay vacant for longer this time of the year.

With that being said, I would suggest holding onto your job at least until your flipping and investment ventures are profitable enough that staying at your job is actually costing you money.