@Wesley W.It’s a gamble to accept a tenant who can’t confirm there income because of tips that are unreported on their taxes.  

I see it as a gamble, not a wise investment.  

While it's true your old home may appreciate, this is gamble much like the stock market and I would not consider this a conservative investing move if these are the only "assets" you have (now if you are sitting on $1M with good liquidity... well different story). 

It definitely felt like a gamble. 

If you want to learn and house hack, that's cool, just make sure you are buying a place that doesn't need obvious cap ex repairs in the near term, or you think it's going to appreciate and you wanna gamble. 

I, too am old enough to have lived through when these adjustable rate loans took you to a worse place than a fixed, however, now it seems no one really considers that an issue, I still say it's something of a gamble.

It's obviously a gamble when you deal directly with the listing agent as they are "making best attempt" to share their fiduciary duties.

Yes, I realize this is a gamble with crappy odds. 

Step one NARPM, step two NARPM, if you can't find any property management company certified by NARPM in the area then its a gamble. 

I see it as a gamble, and not an investment.