The last one was a man in his 80s that was starting to lose his mind.

The 3 key players when starting out in MA are real estate agent, lender, and attorney.

If your home has appreciated in value you can sell it and not have to pay income tax on the profits, BUT only if you lived in it 2 of the previous 5 years:https://www.irs.gov/taxtopics/...So, if you rent it out for a few years you will lose this opportunity to avoid paying the tax man.If you decide to rent it, be sure you want to do it for a long time and be sure you want to be a landlord in general because otherwise you may regret giving up that opportunity to avoid paying income tax on the sale.

Expect investment loans harder to come by, and the credit score and LTVs more strict.Jeff Lazerson of the Orange County Register made some interesting points about this announcement worth nothing:Lenders may lose their appetites to make these loans because of a worry Fannie and Freddie will say no due to their new rental and second home loan allowances.Many lenders “have already increased second-home financing by an average of 1.45 points.

Make sure you are all clear on expectations, decisions, and what happens if the project loses money.For this deal specifically, if it's just a one off with this family member, it might be cleaner to let them keep their $10K and just throw them a finders fee.

Unbelievable really, but I guess that is just the current state of the market and the players in it.  

If I were to get sued in my current situation - I believe the case would have to be above $1.3M before I would have to personally pay out / potentially lose my properties (or other assets).  

@Monica SethNo, for a couple of reasons....1) moving back in for 6 months Still won’t get you to the 2 (24 mo.s) years of the last 5 years (60 mo.s)..you still have that 3 years 4 months (40 mo.) gap in there.Every month going forward, you lose one month that you lived there before you rented it, as you look back 60 months from your  Sale date....so you can’t meet the rule unless you move back in for 2 years.2) If you moved back in for 2 whole years, to meet to 2 out of 5 rule, you still won’t get the full exclusion because you met the 2 out of 5 rule After it was a rental.

I'm working with some investors now who are looking to buy an investment property to simply "store cash" so that it appreciates with the market instead of losing value.

You're on the right track though - just make sure you don't lose site of what your long-term goals are.