Tax Advice Needed (willing to pay): Loans proceeds in S Corp

[Keith Meyer]

I'm looking for some expert tax advice on this situation and willing to pay $$ for it. In essence, we've recently received loan proceeds into an S Corp which is a single-asset entity owning a large commercial property (I know, you shouldn't own rental property in an S Corp. Unfortunately an LLC was not really an option when this entity was formed in the early 90's).

We are wanting to deploy these proceeds to purchase additional investments (mostly commercial real estate). However, we are running into two issues.

1. The lender wants our current entity to remain single-asset. Additionally, we have no interest in adding additional collateral against this loan to the same entity. We would much prefer to invest from an outside entity, as would our lender.

2. We are trying hard to avoid being massively taxed on S Corp distributions, as this defeats the purpose of receiving the untaxed loan proceeds. We could potentially do a loan to ourselves out of the S Corp, however our lender has some qualms with this.

Is there another way to satisfy both our lender and the IRS? All assets are family owned so we're extremely flexible on the entity and agreement structuring.

Please reach out if you have encountered a similar situation and have a potential solution. Again we're more than happy to pay for expert tax advice. Thank you.