I'm so stressed, anxious, tired, exhausted, at a lost...I wrote this long book so that you guys can know what it is going on and will best be able to assist, guide, provide advice. 

If it breaks in 5 years and I have to replace it (as opposed to repairing it), then I have 5 years of reserve to assist in paying for it, and I take the capital loss on my tax return for the difference.It's not perfect but for me, it's easier than tracking everything down to a penny (I press the button to depreciate property for the month in my accounting software and I transfer the expense amount to a savings account for reserves).

And if some sod re-seed is all it took to take the stress of crappy new tenants of him- he was happy. 

In my situation, a December closing would be perfect if I didn't have to make a loan payment for 45-60 days, because I could get the painting, flooring, etc done, before I move in and I would still be in my apartment and not have to stress about moving, as I would have until the end of February.Conversely, if I didn't close until late January or February, I'd have less time to get things done that are easier to do when it's empty, because if lease was up,then I would have to move out, since I wouldn't want to make a mortgage and rent payment (if at all possible).

I have found answers to questions I was preparing to ask by using the search button.

Save yourself a lot of stress, Don’t get yourself in hot water, hire a professional Property Manager

If you can work it out so caring for your mother-in-law does not create undue stress for the family while she lives in an apartment you own I'm all for it.

If your goal is to just have a couple stress-free properties, then maybe it is better to go in with all cash.

After a long and stressful transaction I decided to take risk and move towards Real Estate Investing.

I'm sorry you are going through this craziness and can't even imagine the stress you are under.