It took us from July 2018 closing on it to March 29 2019, should have only takin three to four months at most. 

my general high-level thoughts would be to buy for cashflow and see appreciation as just a bonus, and also to focus on B and C-class assets that will tend to have higher occupancy during a recession.

I'd rather hold it and list in mid March or April depending on the weather. 

Tackle all the major, or potential major, issues from the list your inspector/handyman provided.More is more, not less:  If you continue to spend as little as possible, you're putting a band-aid on severed limb. 

@Michael JakubowskiToo many stories to tell.Presently in process of updating property getting it to sell. (1 March tenant moves out)I have another property in the process of flipping.

I'll be 39 in March and my wife is from China (Guagzhou).

It was on the market for 14 months last time it was listed from March 2015 to May 2016 and sold for $100k. 

Also, I really like B and C property.

I would be telling him he needs to find the full rent for March 1st in addition to all back rent or leave on his own accord at the end of February.

If that takes until March 15th, they won't pay much of a penalty.