Personally I would pick option 1 because you cash flow is already high and so a slightly lower cash flow with higher LTV has relatively minimal impact on cash flow.

Love that you're thinking of how to address the current STR owner challenge and ways to add value given financial constraints many are feeling. 

If you wanted to get some more information on getting funding from a private lender feel free to contact me.Regards,Jackson

I am trying to figure out if I should also max out my own personal Roth IRA in the S&P or just use all my money towards RE.

However, I do think if you can hold out for 1-3 years you might see rates drop a bit and insurance drop a bit, and I feel pretty confident we'll start seeing 3%+ organic rent growth per year in the next 2-4 years again.

Long term fundamentals are great, but personally I'd wait for a few years and see how this multifamily glut plays out before doing anything.

Look for someone who does 24+ deals per year and is also an investor personally.

I've had the same person do my taxes for the last few years, but he seems to have disappeared this year.

Watching BP push Airbnb benefits on here (in my opinion) makes feel a little sick to my stomach. 

Depending on your personal needs from a mentor, you may also want to just start talking with Brokers, Property managers and attorneys in your area.