From looking up on Glassdoor or Indeed I'd estimate their tech salaries to be $120,000 (on the low end) to $400,000+ (I didn't ask them their salaries, didn't want to be too nosey).

I would weigh the new monthly payment of: a HELOC or 2nd position home equity loan.

Real estate investing can be a great idea for several reasons:Potential for Appreciation: Over time, properties often increase in value, allowing investors to build wealth through appreciation.Passive Income: Rental properties can provide a steady stream of passive income, helping to cover expenses and generate cash flow.Tax Benefits: Real estate investors may benefit from various tax deductions, such as mortgage interest, property taxes, and depreciation.Inflation Hedge: Real estate tends to keep pace with or outpace inflation, making it a good hedge against rising costs.Leverage Opportunities: Investors can use financing to purchase properties, allowing them to control larger assets with less capital upfront.Portfolio Diversification: Real estate adds diversification to an investment portfolio, potentially reducing overall risk.Tangible Asset: Unlike stocks or bonds, real estate is a physical asset that you can see and manage, providing a sense of security.Control Over Investment: Investors can influence property value and income through renovations, management decisions, and property improvements.Building Equity: As you pay down a mortgage, you build equity in the property, which can be accessed later through refinancing or selling.Community Impact: Investing in real estate can contribute to community development and improvement, positively impacting neighborhoods.These factors make real estate investing an appealing option for many people looking to grow their wealth and secure their financial future.It really comes down to investing in a growing market, in a good neighborhood & building a great team to support you.

It seems it is so hard to get the positive cashflow in Oregon.

Look at it as a positive thing, this means your making some big moves and need someone on your team who can handle that part for you since your doing so well.

I’ve just begun thinking of exploring house hacking as one of my strategies, so it’s great to hear your positive experience.

I don't think you are in a position to buy anything at the moment.

This creates a potential passive stream of income and a way to extend the lifespan of your coaching investment which seems awesome for your business model.Example: Ryan Serhant, advocates profit sharing (equity stakes) in deals that his coaches help close which takes you from coach to partner, and a model proven successful.Client View: Positioning yourself as a partner to their operation is a way for the client to understand your investment in their outcomes outside of the dollar signs involved, and shows them that you are coaching them in a way that provides long term success.

@James Mc Ree a benefit I was going for was to increase revenue in the LLC, to better position it for funding the next LTR.

With an ARV of $400-425k and an LTV of ~62%, pulling out your initial investment while maintaining positive cash flow around $500 per month sounds like a good strategy.