However, based on our conversation, this strategy might unnecessarily complicate things.As a 1099 contractor, can I deduct all upfront expenses for the STR upgrade, as I did with my San Diego property?

Most of my clients use this strategy.

I am happy to have a strategy chat with you. 

This front-loading of deductions can be advantageous for reallocating funds, but it may affect long-term tax strategies.

Hey guys curious, is it smart to open an llc and rent a room out on my own property just for the tax benefits ? 

I would find some other strategy(ies) to focus on that give you experience and value in the market. 

Hi Hunter,Have you considered using strategies that rolls over the cash quicker like STR, flips or BRRRRs?

Unless you totally threw all REI strategies out the window, which I highly doubt since you are getting into the weeds of Def Comp, you will blow that 457B out of the water in due time.

@Julia FranceI recommend a consultation with a real estate tax strategist to learn, develop and implement tax strategies available to real estate investors. 

Most folks here on BP would be quite happy with a 15% Cash on Cash return if all we had to do was write a check.My strategy for that:1.