Even if OP can complete a purchase in Cleveland with $23K, aside from valid concerns others noted about reserves, is the risky asset in a distant market really the best place to invest?

If you are looking for loans on real estate or a business lenders don’t necessarily care about the credit history of the LLC - they care about the performance of the asset and your creditworthiness since you will most likely have to sign personally.I have established multiple LLCs just days before closing on large loans for different assets, those particular entities barely existed and the banks did not care.If you are talking about pulling a business line of credit (like a HELOC, but against your business equity) then the banks like to see some history of revenue.

So i have pretty sizable personal assets, along with a relative high income. 

Their representative recommended I engage with JP Morgan Chase private banking / wealth advisor as they thought this would allow them to be more creative and include other assets as part of the collateral.

Instead of this, I find it more helpful to look at percentile performance across the market for a specific asset type, and also to check comps.

My argument is simple—real estate, unlike most assets, doesn’t actually lose value over time.

The lenders I have seen that will cross properties as a second lien are generally strictly hard money or asset based. 

We have assets for sale in rutland vermont that are closer to the 2% rule. 

Sponsor has executed this strategy multiple times, management company specialize in this kind of asset-Does the Asset support the business plan?

You would be in a losing asset.