One option I'm pretty familiar with is land conservation easement/fee simple - though this is more of a strategy to help with all AGI rather than strictly capital gains.

Here are some financing options to consider:HELOC or Cash-Out Refi on Another Property – If you or your mom have equity elsewhere, this could be a more flexible and lower-interest option.Business Line of Credit – Since the property is in an LLC, you might qualify for a business LOC, which could cover construction costs.Private Money Lender – If you’re okay with 12-15% rates, a private lender could fund this as a short-term loan, especially if the guesthouse will generate strong income.Construction Loan – Some lenders offer short-term construction financing, which converts to a longer-term mortgage once completed.Seller/Partner Financing – Bringing in an investor or structuring a joint venture with someone willing to fund the build in exchange for a share of the income.Credit Card Stacking or Unsecured Business Loans – Riskier but could work if you need to bridge a gap until the unit starts cash flowing.Would love to hear more details—especially your timeline and expected rental income.

The planning staff should be able to walk you through any options for zoning changes or variances if there's a way to make short-term rentals work in your case.

I would like to find a way to generate additional income and am exploring options other than having a long-term roommate.

This way, the lender wouldn’t be triggered (since most allow transfers to a trust), but I'd still have the benefits of an LLC.Other options a.

@Ana Vhan there are many commercial options where you can add multiple locations/multiple states onto a single policy.  

I'm assuming if this was an option everyone would already be doing it but I am just curious from a professional to understand why this isn't an option.I received a question from a friend that was somewhat similar to mine above which got me thinking. 

If that's what you're really after I would start with the basics of what kind of bank loans either residential or commercial are available to you - not saying this is the best option, but it's a good place to start.

The mid-term rentals are also an option.

Also, I've always wondered why arbitragers don't negotiate an option to buy upfront?