Part of my luck I guess has been buying in strong school districts and mostly B type property, I feel I would have gotten burned more if it was C type.Agree with you on approach, I have been strict with application requirements and have a high bar on credit score, etc.

Strictly my opinion ...No, we're not in or approaching a "bubble".We ARE, however, in a housing shortage.This was predicted just after the crash of '07 / '08 when some 80% of builders and developers went under.

I know the 15yr rates are better, but the interest difference seems a small price to pay to gain a few hundred dollars or so per month of spending power.I too like the approach of using a HELOC on my primary, rather than a cashout, as the bill is separated off, as I don’t pay for money I’m not using, and as the LTV can be above 80%.

The numbers you shared aren't great from a cash flow standpoint (no offense) and I think if your plan is to unlock the equity you have by selling, pay off debts, and buy a multi to house hack, that would be a better long term approach then hanging on to the townhouse.

@Evan O'Brien- I'll try generalize some of the steps I take, however each person will have their own unique way of operating.I take more of a top down approach.

If so, how would you recommend I approach certain real estate agents if I come across a good deal and a have a buyer ready to purchase for a lower price?

My friend approached me about investing in rental properties together.

Dan, your first thought, consulting an attorney, is the right approach. 

Good ROI/IRR with long-term appreciation approach.

In short, the trust would be looking at approaching $400k in capital gains taxes.One of my big questions is - when my mother in law dies, does the trust receive a step up in basis on the properties?