Looks like you will be adding in something like a "no firearms are allowed to be discharged on the premises (except in life threatening self-defense situations).

Where you put the work in will change if it's not more capital you'll be adding time and skill.

Within the next few days I will be adding posts on (1) issues on financing legally non-conforming properties; (2) rezoning a property with zoning problems, such as the property you mentioned and 3) what happens when a legally non-conforming property burns down?

As I mentioned, my main goal now is to actually figure out what taxes would be on a potential 600k sale to see if 1031 is worth it. 3% realtor commission is 18k so thats pretty good if it can be added to 1031.

Yes your Heloc + Mortgage for the first home will be added to your DTI, however if you have a tenant in place that covers that amount (contract for at least 12 monhts) you might be able to write it off... 

I'll be adding on housekeeping twice a month (at my cost) and weekly trash pick up.  

If you were not, you’d save the same taxes as strategy 2  Or 2) You’re going to spend money (capex) that will be added to your cost basis giving you a higher yearly depreciation.

Will you be adding them to your site?

*There are term insurance riders that can be added to a whole life insurance policy.

I'm thinking that Environmental be added as an endorsement under our general liability insurance might be a better way to mitigate risk?