Okay. It has taken me weeks to get through this whole thread

, and now I'm excited to participate!
I was wondering if I could get some thoughts on an issue I've been grappling with. I am late to the game in terms of making wise financial decisions, so at the age of 48 I don't own a home and still have $30k in student loan debt. I also have $300k in a 401(k) and $60k in savings. The one thing I have going for me (other than the fact that I have learned some hard lessons and believe I'm now on track) is that I will have a pension of about $4200 per month if I retire at age 65. (I love my job so the thought of working at it another 15 years or so doesn't bother me.) I am also maxing out my 401(k). I have not yet starting funding an IRA (Roth or otherwise).
I would like to have a paid-for house when I retire, but the problem is I don't know where I'll be living. I will definitely not be living where I currently live (CA). I have owned two homes in my life. One was a financially positive experience, and the second was an absolute financial disaster. So I still have PTSD from that experience, and am leery to buy something where I currently live (which I could afford because it's not one of the HCoL parts of CA) on the (possibly false) assumption that I'd be able to sell it without losing money when I retire.
One option is to buy something in my home state on the East Coast, where I would almost certainly be living at least part-time when I retire. The rental market has always been good in the area due to nearby universities and coastlines. And, my brother in law currently takes care of the rental units he and my sister own in the area where I would buy, so I believe I could hire him to look after mine. This option also appeals to me because it could allow me to indulge my wanderlust in retirement - I might be able to continue to rent the house for periods when I was away traveling or visiting friends/family.
The other option is to put all the extra savings (after maxing out the 401(k)) into an investment account, and as retirement approaches and I have a clearer idea of my post-retirement plans, start to move some of it into less volatile holding accounts and buy something outright at retirement.
I have previous experience as a landlord, but that was when I was in Boston and the property was in New York - not like owning/managing something from all the way across the country (but again, there are people in the home state I could rely on.)
Does anyone have any thoughts? Any important factors I left out? (I am a SINK and although I hope that changes at some point, I need to plan as though it would not.) If I went with option 1, I would make sure to only do it if I had a nice healthy emergency fund that could cover the mortgage and the CA rent for 3-6 months if disaster struck (like I lost both my job and my tenants at the same time.) Which likely means I wouldn't be in a position to buy until at least a year from now.
Thanks all!