The second home loan guidelines directly state "The Borrower must keep the property available primarily (i.e., more than half of the calendar year) for the Borrower’s personal use and enjoyment"This means that you can only book it out on STR platforms for half of the year (50% max occupancy), which really sets a cap on your max income. 

@Edward Suess-HassmanTo make sustainable investments, set clear goals, research markets outside the Bay Area, consider creative financing, learn from others, build a strong team, and use educational resources.

•Continue tracking expenses and maintaining organized accounts.4.Grow Deal Flow:•Use a small portion of your credit for marketing campaigns (direct mail, Facebook ads, etc.) to source deals consistently.

If you're in the real estate investment business and must watch every penny, irrespective of your time, then by all means, do what you think will keep your expenses to a minimum.If, on the other hand, you are really in the business of creating profit by way of being a good marketer and a committed dealmaker, your creative energies ought to be reserved for doing what you do best (or intend to do best)...

Also who wouldnt want to work for an hourly wage, under the direction of someone else without the hassle of buying and transporting materials or the responsibility of permits, inspections and the like.

Even if you don't feel you have enough info to give me directional advice, how would you go about deciding whether to address the problem?  

Because significantly less than 100% of your investment actually goes into purchasing or improving the property, and the property is purchased at retail value (or worse), your returns will badly lag any benchmark of direct property investment.  2.

What are some unconventional creative financing strategies you've personally used or encountered in real estate investing that led to unexpected success, and what lessons did you learn from those experiences?

There are other creative ways to get this done.

Yeah, honestly not much creativity right.