Comes down to mitigating risk and what your comfort level is.

Again as an example, the benefit is a regular monthly income in retirement, the risk is that the cost of ownership will be more than the revenue (mitigated by using only 1/2 the HELOC so a lot of capital remains), and the tradeoff is that I am leaving money on the table by paying off the mortgages in 10 years (to increase cash flow) and that by using a property manager I am hands off, but I am not maximizing returns.  

You could stretch your capital much further by leveraging that capital.Personally, to mitigate risks and make it more approachable I always recommend starting out and going deep in your neighborhood market.

It's generally a good rule to continue to get more doors as you mitigate your risk from vacancy, damage etc by spreading it.

This is a common and acceptable method of mitigating asbestos.

I’m considering holding a certain property to sell till June to take advantage of this higher summer price, but I’m wondering if a wave of evictions in the first half of 2022 is likely to add inventory to the market, thus substantially increasing supply and so mitigating or reversing the usual May-July price jump.Any data, experience, insight, or corrections of mistaken assumptions/data on my part is appreciated!

The more details that are set upfront, the better chance all parties can mitigate challenges with the partnership. 

The HOA is in search of an insurance company that is experienced with packaging wind mitigation, liability, general, etc. all in one portfolio.

If you have a middle score below 600 that doesn't give a lender the greatest confidence in your ability to repay, but if you have loads of experience with that score below 600, you should have no problem getting a loan with max leverage @ great rates because you have a proven track record to mitigate that score. 

The idea was brilliant in my opinion but after further evaluation once we got the 4pt, home inspection, and wind mitigation we found out the duplex hasn't been updated since 1972 when the duplex was made.