.- I would try to reduce your number of questions.

I upped the ARV to $750k after putting $110k into the rehab, and am still seeing no cash returns for a decade, which is not ideal for scaling..I know that the private lender route is likely a road to faster returns to reduce my monthly costs, but I'm trying to find a path to having a couple deals in the portfolio before bringing on anyone else, more of a courtesy for limiting exposure/liability, create a track record, and building company value.

If you find it works out for round 1 you might get the traveler to extend their stay and reduce the turnover time.  

Whichever you choose should get you started and then you can go into your proactive outreach from there.

Pulling in a 12% return on an initial investment in a rental property can't be compared to an investment account that is reducing your tax base, reinvesting dividends and most importantly- compounding.I am not knocking one over the other, I have and love both, but they are 2 vastly different vehicles.

There are some very good deals to be had here and your risk is also reduced.

If we can increase operational efficiencies, we can reduce our expenses.

@Lilach AdoniMany of the properties attached to country clubs have restrictions on rentals and/or transferring your membership amenities.It is worth looking into the financial viability of the country club itself; the developments with many houses and forced membership with mandatory transfer fees seem to do better than the boutique clubs with far fewer homes and/or optional membership.Also, keep in mind when you go to sell, the buyer pool is drastically reduced and generally makes these properties less liquid.

"Little" is relative to your market... for example in many California markets, you will pay to live in your  house hack, but your cost of living is reduced significantly.

He's exceptional at proactively creating terms that mitigate our risk and protect our investors AND getting all parties to come to the table, work through challenges, and get the deal done (it's no surprise that not all deals are smooth haha!)