That may be, but Chicago and Cook county are EXTREMELY tenant-friendly hell holes as far as landlords are concerned.Don’t move to a place because of its laws.

Hi Carlos, since best option is off table and now you need to look for a new buyer maybe try relisting it with an agent who has good network and understanding of what the goals in this transaction are. you never going to get the dollar-to-dollar value that you put into the property, and we are not even considering the time and headache.

But I know this is a 2-3 year from now goal for me, and I just haven't been able to find much on actionable steps to be a in the driver seat on a deal like this.

There are so many investors, lenders, agents and other professionals you can meet here that will help you get one step closer to your goal.

Again 20-30% is fair.I have an almost 100 year apartment building where I pay some of the utilities. 60% is a fair estimate and it's often more than that.I have a couple of older houses in 'bad areas' where the tenants regularly trash the property causing thousands of dollars in damage and move out in the middle of the night.

If the landlord is able to re-rent the unit then the breaching tenant will no longer be responsible for the rent once the new tenant moves in and begins paying rent.

Cash flow is better here, but appreciation is less (CA is off the charts for this metric compared to most of the country, so it's not that OK is bad- depends on your goals and expectations). 

Overall I feel your goal should be "just enough" to make the prospective (most typical "opportunistic") trespasser move along and find an easier target.

The sales price is contingent on the property appraising for the agreed-upon value in that given timeframe.The goal of subject to, for the buyer is to take advantage of your low interest rate, maximize profits to pocket as much cash flow as possible, and then, however, in many years be able to cash out refinance and pay your mortgage off in a lump sum to acquire full rights of the property.

Move into the triplex for two years and use IRS Publication 523 Sale of a Residence to not have to pay some of the Cap Gains when you Sell.