I’ll second all of what @Keenan Fitzpatrick just said. There is great value to simplifying your life so you can focus your efforts. If you look at your total picture, I think that you’re actually going negative each month:
+$500 cashflow from your duplex
-$500 credit card payment
-$200? Other debt payments
-$250 property management in AK since you don’t live there.
OR
Sell the duplex while the market is reasonably good, pay off all of your debts, and have $54k in savings for a down payment. That should get you into striking distance for a triplex like you mentioned and significantly improve your debt to income ratio. You’ll also reduce your personal stress enormously, which is important too.
Colorado is hot hot hot right now, so I think it’ll be difficult to cash flow unless it’s a house hack. Even then, you’ll probably not be completely rent free. I’m in the opposite situation as you are, we just helped a friend renovate a rental he’s owned for years in Westminster and I had the option to buy it at cost and keep it as a rental. The initial offers all came in so far above asking price that it makes no sense to buy it. It was on the market less than one day and should be a quick closing and we will do better investing back in Alaska.
Best of luck to you in whatever direction you decide to go!