Ricardo, I love that you are thinking of the community and trying to balance out all options.

This could be done through a "subject-to" deal, where the buyer takes over payments on your existing mortgage while you provide financing for the remaining balance.

Also need to focus on markets/communities that strike the balance of relatively low land cost, strong rental demand and include professional property management to strategically minimize vacancies and maximize rental income from day one.If you have more questions, feel free to reach out!

This way, you’re not at risk of losing all your hard-earned feedback and visibility, which could set you back in the competitive short-term rental market.It's essential to find a PM who can work with you in this setup, as it's a balance between functionality and maintaining your property’s reputation online.

I count the position in this deal as a $0 on my balance sheet. 

Stessa is great if you are an individual and you are just trying to track the income and expenses on your rentals.Unfortunately, for Stessa, they do not have the ability to generate a balance sheet which makes it a no-go for any business.

I have been a passive remote landlord throughout the time, thanks to my agent and nice tenants over there.We have almost enough cash to pay off the remaining balances of the mortgages but obviously we want to use it in a different way.

The HOA, had a balance of $195k at the beginning of the year and is expected to have $207k by year end.

A balanced approach might be best: consider contributing to your Roth IRA to ensure you're benefiting from its tax advantages, while also starting small with real estate investments that require minimal capital, such as house hacking or partnering with other investors.

You'll be able to take out half of your vested balance though, so not a ton.If you liquidate it, you're going to have to pay 10% (assuming you're under 50 years old) + taxes owed if it's pre-tax.So maybe a combination of the two using a HELOC on the equity.Is the 401k in the Roth portion by any chance?