kudos to you for starting your Stay healthy journey.As many have already repliedsleep, movement (your cycling), weight training (muscle mass decreases a you age) , keep challenging your mind, maintain your social circle, diet - loose sugar and processed food.If you do the above you are way ahead of most folks. 

Whichever strategy that you choose, run your numbers, and definitely consider all the other benefits of owning real estate i.e. appreciation, loan pay-down, potential housing expense decrease and/or cash flow. 

We are seriously considering this to decrease inheritance tax as shares in a property are considered differently in RI for inheritance.

That may sound pretty good...until you discover that their net worth is decreasing at a rate of $2 million per year, and they've got $100 mil of adjustable rate debt on a portfolio of D class properties that forces them to work 80+ hours per week just to keep the whole thing afloat...Investor B tells you "my net worth is $1 mil" --to many successful investors, that sounds like a relatively insignificant net worth...but, investor B owns a portfolio of A class properties with zero debt, professionally managed, their cashflow is $500k per year, their net worth is increasing at a rate of $1 mil per year, and they only have to work about 1-2 hours per week to keep their machine going.Personally, I'd MUCH rather be investor B than investor A, even though investor A's net worth is 10x of investor B's.So yeah, tracking net worth is advisable, but it's only a small part of what an investor should be tracking and modeling, and net worth alone might not be very indicative of an investor's success.

Take advantage of that.Hiring contractors will decrease the profits you would make if you had done those projects you were able to do yourself, but it will also shorten your holding time.  

What we see problem with multifamily syndication is really a math problem rather than syndication problem.If spread is negative than the chance of investment poor result is obvious.It's similar like if you buy company stock at three year high, but their forward looking order is decreasing without new product.

If house hacking can decrease your monthly housing expense, then it can be very beneficial in the long run.

I would be very surprised if this was accurately done.That means you are cash-flow positive after depreciation of $1,666 per monthIf the return was filed, you may want to pay another accountant to look over the return to see that it was done correctly.Yes, buying another property, given today's condition of high prices and high interest rates would likely decrease your rental taxable income.

The reason I am selling the Condo is to pay off some personal, and unexpected debts of about $18,000 to decrease my DTI to help me qualify for my Dads VA loan (they want to move to Texas), which is a 3BD 2BA single family home. 

I'd take another 200K and just dedicate to my own fix and flips here in Indy.I'm a car guy and I'd take 100K and dedicate it to flipping old muscle cars which I have a history of.I'd take another 100K and put it some deals as a LP.Then us the reserves as needed