Those have multiple plusses -- tax advantages, a forced health savings account, tax-free earnings forever, and frankly you can only contribute but so much per year.  

1) Are you planning on self-managing forever or giving it to property management in the future?

Here's what I get for different rates of return:If he got a 5% return he'd have:$12,682.22 from option 1, $28,599.92 from option 2 for a difference of $15,917.69 at 15 years.If he got a 10% return, he'd have:$26,723.52 from option 1, $44,348.33 from option 2 for a difference of $17,624.81 at 15 years.At a rate of 10%, the difference between the two options reaches a maximum, and the difference then heads towards zero, with the two options being equal at about a 20% rate of return and then forever favoring option 1 (the no closing cost) for rates of return above that.

Don't think it will last forever.

Of course, do this as fairly and gently as possible especially if they have been renting there forever.

He does provide great information that I am forever grateful for.Look up home possible matrix from Freddie Mac. 95% LTV on 1-4 Unit. 

The 3M purple sandpaper will last practically forever in this application and do just fine sanding both "easy sand" types of joint compound and regular joint compound. 

#3 - Each area has a different avenue that investors can capitalize on.South Odd numbered Streets: STR and LTRs, Excellent cash flow, less appreciation, less profit on a flip.Historic District - Opportunity for Great Cash flow( Multiple units), great profit on a flip, the downside is that some areas are run down right outside the historic district.Canyon Creek / Western Hills - Perfect for Flips, 1970-1990 properties that need to be updated, desirable area for a "forever home", Opportunity to make a very good return on a flip, A higher PP means less cash flow but will likely have less vacancy and a more stable tenant, less opportunity for MTR or STR although this is still a good area to try it.

I got stuck in the analysis phase for what feels like forever thanks to the majority on there - BRRRR or nothing.

Your goals with your primary residence matter (how soon you want to pay off, is it your forever home, etc.).