Probably 8%+ mortgage interest at 40% down to make a safe assumption.

An experienced broker with lots of choices at the palm of their hand is probably the best bet.

Better safe than sorry!

Since my son knew how to do it safely with ropes and harnesses he made like $3,000 in 2 days! 

I’m not a betting man.

If you are close to retirement and are accredited, it's safe to assume that you'll likely have some decent, taxable income rolling in during retirement.

Best bet would be a “partnership” with a monied individual looking for a high risk/high return passive investment with you providing the “active” part.  

Quote from @Brandon Foster: Hello Ryan,STR is do able in the north county area but there are a lot of rules and regulations.The city of Oceanside right now will not allow anything STR unless it’s west of pacific coast hwy.This is changing a lot too so you need to be aware of that in your plans.Carlsbad is super strict too but there are some condos that are still available to do STR in.Medium term rentals are as safer bet but way less profitable.

But if they gov't changes to a 90 day minimum, you would have to operate as a 90 day rental or longer.And talking to local experts, if you want to own a STR on O'ahu, your safest bet is to buy a unit in a Condotel that is located in the "Resort" zone of Waikiki.  

I can put up with a 1-hour work commute or a little more if it means having a house in a decently safe area.Other Info:Credit Score: 700s (due to student loan payments)Monthly Income: $4600Work Location: I commute to Northern Virginia and D.CGuys, I could really use your help or recommendations on what you would do if you were in my situation:Location: I'm thinking somewhere in PG County MD due to my commute, like Hyattsville MD.