As with any market, there are risks and rewards.

With reward, there are always risks involved.

Add the financing challenges and that you existing structure likely will become rent controlled.  

First of all, congrats on taking the leap into vacation property investing—it’s such an exciting journey, and I promise, with the right guidance, it can be incredibly rewarding!

Every great business that has ever existed had a Visionary/Integrator relationship of some sort.

As you grow your portfolio, keep an eye out for lenders who offer low down payment options for investors or those that allow leveraging the equity from your existing properties to fund new ones. 

It sounds like you have an un-permitted unit, which is essentially always a risk since there has been no notice to the AHJ that it exists and they can therefore initiate a code case to have it removed in most cases.

Transitioning from construction equipment rentals into full-time real estate must have been a big step.I can relate to your passion for finding deals and helping others reach their goals—it’s such a rewarding aspect of being in this industry.

Two, you'll have a much easier time obtaining a mortgage product if you have a track record of W2 income.In the meantime, continue implementing the strategies you mentioned: save religiously, build your credit, pay any existing debt owed, etc.

Zoning Ordinance ExceptionsSome properties in the target zone don’t meet the minimum lot area or width size requirements under the zoning ordinance, yet houses exist on smaller-sized neighbor lots.How could these properties get approval for development?