Sounds like you are heading down a complicated road for maybe no reason.  

The higher HOA and insurance fees have made investing in condos more complicated and not look quite as appealing, but there are still condos that can be purchased and an owner should be able to cover the cost of ownership.

Michael blurry, made famous by the greatest short, personally only invested in us treasuries despite making huge amounts of money doing complicated trades and having a deep understanding of us equity markets.my experience with windfalls is seeing cousins with large inheritances.

I borrowed an underwriting model from a Real Estate Private Equity professional and it seems a little too complicated for what I am doing now and what I plan to do in the future.

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

In Colorado, there are increasing regulations on STRs that make it more complicated, but it's still possible and can be profitable.

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

@Mark C. for full anonymity, you'd need a Wyoming or Delaware LLC, but that can get expensive and complicated.

In most cases, neither is warranted.Warning: I am not an attorney, and this can be a complicated topic.

Don't make it complicated.