Honestly, I've given up on finding cashflow anywhere close to the city due to rates and prices, BUT some other opportunities you may want to consider are:Live in flip - mentioned earlier in this thread, always a solid option in any market.Condo conversions - good money to be made from this and since they're a little trickier than a traditional flip there tends to be more inventory available that would allow for a profit.ADUs - come February 2nd, ADUs are allowed BY RIGHT on any SF property in the state, owner occupied or not.

Maybe he's the exception.But the good news is - no matter what you do, if your brother just leaves it all as "passive" and doesn't mess with anything, whether short term rentals, or traditional rentals - the right tax planning could mean a box of his investment dollars that is effectively able to grow tax free. 

Is this all handled by the PMS and then routed to the guest by whoever is the primary host?

My primary focus is on maximizing cash flow.Does anyone has experience with STRs in Aspen, I’d love to hear your advice or insights!

I've also used traditional loans through regional banks and a few SBA loans. 

Going in, I have a HELOC that I can draw about 60k from my primary and then 25k in cash.  

Hopefully in just a few years the cash flow can help fund your Primary rehab and enlargement.

This would also be where an appraisal would be ordered in a traditional sale, but if using a hard money Lender, they have probably already evaluated the value before offering you terms.5.

I spent 5 years buying 5 primaries and 5 rentals.

I have landlord policies for my rental properties in TX and AL states, but I am not able to get an umbrella policy form my current insurance company, because I do not have car insurance and primary residence in US, as I am not a resident in US.