I have been studying for my real estate degree for the past 3 years and would love to get my feet wet.

Yes, you aren't taking advantage of the better financing options available for homeowners, but that's only one of many things to take into account when investing in real estate.California is also a really tough state to invest in; high prices, unfriendly to landlords, etc.

There are STR specific DSCR loans that account for the previous revenue if you are buying one that has been going already.Read Avery Carl's STR book from BP and also follow Bill Faeth, Kenny Bedwell, Taylor Jones to start with to get an idea of what is happening in STR right now.

Study the market.

That would be around $90,000 sitting in a savings account!

If you pay rent while in Aspen, that housing expense will be factored into your DTI ratio (e.g. total rent paid in 5 months divided by 12 months).You should be prepared for your loan file to go to an underwriting manager for second-level review on account of the occupancy risk associated with your primary home being located so far away from your work.

We currently have a LLC that owns our existing rental property and we run the short term rental activities through this LLC with its own separate bank account.  

Study the market.

Or if that’s not allowed sell it to a friend who will then sell it to my personal IRA at a discounted rate so when I turn 65 and sell the properties , I don’t have to pay any tax on all of my properties assuming I don’t sell them until they are in my IRA account…

One thing that makes me always feel better about debt and leverage is a good breakdown of your tax return with your accountant.