Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is likely to be higher, then you may consider an umbrella insurance policy.

I'm interested in understanding from others what they consider an acceptable timeline for payback of an all cash rental purchase based strictly on the anticipated cash flow. 

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is likely to be higher, then you may consider an umbrella insurance policy.

Definitely consider an option that allows you to achieve all of these steps in one place (ie. keep track of things like rent payments + leases, but it also offers several other tools as well -- the ability for tenants to build a credit score up to 40+ points for on-time rent payments with our CreditBoost feature; which can be enticing for them as they are new student renters); and lastly offers maintenance ticket tracking with automated messaging).

So if you could take $100K in today's market, would you invest it in another rental property or would you consider an alternative investment?

If it's truly a D- neighborhood, it's too risky for me to even consider an 8 CAP property....You need boots on the ground for these types of investments, there are too many ways for it to go south on you in a hurry.

Any other alternatives; is this what one would consider an attempt to raise private money? 

If it is a short term hold, you could consider an ARM loan or an interest only.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is likely to be higher, then you may consider an umbrella insurance policy.

Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is likely to be higher, then you may consider an umbrella insurance policy.