As you age and your cash value accumulates, the risk is shifted from the insurance company to you.

It would be a wrong timing to all in your money today, top of cycle, seller market.At today top of cycle, today seller market, unless you still have plenty of cash to buy more properties after it, then it may be ok to buy a rental today, and lose some money on this property, then use more cash to buy more properties after it shift to buyer market, so you can break even and make more money using the properties you buy in the buyer market. 

I had a mind-shift years ago that I focused only on closing as the win, but soon realized the process and growth along the way was quite rewarding.My first probably 15+ offers failed in my beginning days of investing. 

Mid-income level, maybe slightly shifted to the higher side.

I'm sure it can't be easy.Maybe hand it off to a property manager and shift the blame to them?  

I highly recommend always buying for cash flow first,  so you are protected if there ever is a shift in the local market economy. 

Listing are often misleading...in some places the MLS itself will pull the SF data automatically from the county records...I recently visited a house which was advertised as 3BR/1BA with one photo from the outside...infact it was a quite spacious 5BR/1.5BA...I doubt listing agent was even once inside...on county records house showes as 3/1...Please let us know what you end up doing...this was one of the most interesting threads lately.

Good news is that we have been seeing good appreciation over the last years and will continue to do so, so the shift in demographics keeps fueling the invetory shortage, which drives up prices with no reliev in sight.

Make a system for this so the steps are automatic next time this come up.Do you have pics of the unit already?

@Syed Hussain - Did you or your tenant opt not to extend the lease or did the lease extend automatically for another year or month-to-month?