Wow, that's impressive! I hope that we'll have our home paid off in 10 years, then I can crank up my retirement funding to around 40-50%! I'm over real estate after renting our Fruita home out for several years, we bought low and sold high and made money, but it was a headache dealing with mechanical breakdowns, renters personal issues, late or no rent, evicting someone and cleaning their mess. Yeah, I'll pass.
We have little debt, my Jeep is almost paid off... all other vehicles are paid for.
We've been very fortunate with our jobs and some investments we've made or been "given" over the years. We don't take it for granted to be in the position we currently are.
We helped my mom for a period with her rental and the experience was much the same as yours. When we finally got the last renters out, we had to gut the place (down to the studs) and redo the entire thing. It was absolutely disgusting. I won't ever do a long term rental. My wife and I have thought a lot about doing vacation rentals. We've thought about doing something in Hawaii and something in St. George. Both places we go a couple times a year and almost always end up staying in the same general areas. it would be nice not to have to worry about a place to stay.
I like the idea of the Roth IRA, I know Catherine has one that she started years ago. She's also a teacher paying into PERA and actually needs only one more year of teaching in California to be vested, so she could draw there, too. With my RR retirement, she will also draw 50% of what I'm taking home at retirement. Unfortunately, UP doesn't offer to match or do anything else with 401k's, which sucks.... but this is on top of my RR retirement. I've been paying in for almost 15 years now, need another 15 and then 60 yrs old to draw.
Not sure what you and your wife are making, but you may or may not be eligible for a Roth IRA. (you have to make less than $189K or less between the two of you and you can only contribute $6K a year) You also have to consider when you want to pay taxes (now when you're likely in a higher tax bracket, or later when you're in a lower bracket). Also, if you're not maxing your pre-tax, you should do that first to lower your current tax obligation. There are many scenarios that Roths make sense, just make sure you understand them before jumping in, your money could work harder for you elsewhere if you aren't careful.