Are there any simpler loan options I should research as I start thinking about our next property? 

When it comes to a lifestyle property, it's another ball game and all the comments you wrote make total sense, especially for people who like similar things in life.

While they only took up a word or two of this story, they took up months and years of my life for which I earned nothing and lost much, at least in the short-term.

But from what I have seen it has a lot of useful accounting tools that should make my life significantly easier, and ultimately that's what my intent is.

I've done it twice in Reno, NV and it's changed my life. 

I wouldn't bet my life on 50%, but I would bet they are more problematic than the typical long-term renter.

My mom is nearing the end of her life and has left me and my two brothers her condo in Hawaii.

I think every market and every person have their own reasons, but here are some thoughts from a property manager.Pros for self managing / cons of PM- Keep all the revenue- You have 100% control- You own listing, photos, etc- Nobody will ever care about your investment as much as you do.Cons for self managing/ Pros for property management- This is a 24h / 7days a week business and I imagine you have at least somewhat of a life I imagine. 

It was kind of a bad spot in my life at the time.

They have to take it out within 10 years, add it to their regular income, and pay taxes at the highest bracket in their life.