Primarily, when will this end, and when will things start back up again.Which seems to call for decision-making in the face uncertainty (because there seems to be a gamble element to it), like happens in war on the battlefield sometimes.Except your not really at war with the tenant.

The tenant has a scratch-off lottery ticket gambling problem and often comes home with "many"  tickets in his pockets.

I suppose you could gamble and hope that your operating expenses are lower than 40%. 

It really depends on how desperate you are to sell quickly- you can definitely save money, but it’s a bit of a gamble.

It seems like a gamble purchasing from just viewing the outside.

Real Estate is where it's at.Stocks are basically gambling because you have no control over them.At least in Las Vegas they give you a buffet and free drinks.

Now I know this is a huge huge gamble, and it is a negative investment initially but I am bound to my clients here in SD for at least the next 3-5 years and doing the math if I continue to rent at SD prices, I can see clearly how I am not paving the path to any kind of financial freedom and I am not taking advantage of San Diego's tremendous appreciating market. 

We are often paid to be more conservative, than gamble away our clients wealth on any big bet. 

Many offshore VA’s can handle this in a couple hours at no more than $10/hr.

Just as you should only gamble with money you are willing to lose, you should be only be investing with money over and above your savings.