Just asking to clarify how the future value (for the cash out refinance) will be valued.

One of the main challenges is that I can only afford to put 5% down, which would leave me tied to this property’s expenses for the foreseeable future, making it harder to pursue other investments.All of this said, I’m really struggling to stay positive about investing right now.

Using more of your own money decreases your liquidity, making it harder to qualify for a future loan. 

But don't feel locked into formal education if your main goal is to get into investing, often the best lessons come from doing it.Feel free to reach out if you need any advice on financing your house hack or future investments.

Maybe in the future I would just suggest having the documents digital and on a computer somewhere. 

The future is bright for you. 

If your income exceeds $150,000, your ability to deduct passive losses from rental properties is limited, and any disallowed losses carry forward to future years under the passive activity loss rules.Yes, the deductions can accumulate and roll over year after year.

Securing a lower fixed rate now could hedge against future rate hikes.Conclusion:If your plan is to hold the property long-term, buying the rate down to 6.375% makes a lot of sense.

Would switching the property to my LLC help for looking for future investment properties?

Moving forward, I’ll make sure I have a buyer’s agent in future deals.