The bank has no emotions, that is a positive IMO.

I'm obviously trying to get you to remove the emotions you've attached to this particular property for these two decisions.

However, if you sell now you basically get the first part of that equation as tax free, however, you'll want to know your transaction costs and do a cost-benefit analysis.If you're not emotionally attached to the house, I'd sell the house now and find an investment that aligns with your goals.

Once it happens, there will be 2 types of investors, logical ones who stuck to solid numbers and ensured multiple exit strategies and emotional ones who ignored all the numbers because they had to have this dwelling because it's in a neighborhood with a good school.

You just have to keep going.Probate can be good but you are dealing with the wrong kind of emotions, either they cant let go, or are too greedy.

Personally, I think linking with an agent and renting these houses out would fit the needs for most temporary residents.

It has nothing to do with emotion or heart.

The tiny house cost is over and above this.This approach costs more than most tiny house advocates want to pay.I think perhaps there should be some options for temporary foundations and temporary utility hookups in the zoning codes.  

Purchasing a property is risky and to get $3600 cash flow over the year it doesn't seem worth the headache.Of course if your goal is to reach retirement as fast as possible and you don't want to stay at your high paying job forever, or the income may be otherwise temporary then yes I'd take the 40k and get the first rental.

The problem with clearing it with a water jet and using root kill is that this will be only a temporary solution ... the pipe is compromised and the roots will come back.