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.

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.

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.

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

I appreciate the info provided so far, but I have more questions and I don't expect freebies from pros like yourself.I'm looking to get together a semi-solid idea of how this all works before I drill down, in depth with my usual accountant in a couple weeks (if I still decide to drill down with my usual accountant after learning more info on what I'm trying to do - from you or someone else.)My usual guy can't get to me right away and I'm in a time crunch, if this deal is going to happen the way I want it to (bonus depreciation decreasing by another 20% on Jan 1st)I really just need to understand Bonus Depreciation, in detail, and as it applies to my situation.I'm brand new to all of this.

Higher maintenance must be accounted for and is annoying, but if you end up refreshing it before renting, that will save you time and money down the road.

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.  

Account Closed not sure what you mean?

There are some exceptions to that as I mentioned that have been done in the past, but again that would be through an escrow account, etc.

Not only attorneys, but accountants, architects and other professional service providers.