I have not done this with vacation property, but I did do it with commercial investment property.
First, we got the group together. I was one of the last ones invited in. There were a total of 12 investment units. I had a full unit. Some investors had 1/2, some had 2. We chose the property in which we were investing and did a purchase and cost analysis. We figured out the loan amount, taxes, insurance and extra for refurbishing (we were rehabilitating property and the refurbishment was the most significant costs).
We formed a corporation and the initial investment in the corporation was substantial, but not hideous, about $5000 per investment unit. Most of the initial investment was used for the down payment on the property, the balance was placed into reserve. We knew what the monthly payment was on the loan before investing and we agreed that we would each put an exact dollar figure in each month as our contribution. The monthly contribution amount was sufficient to pay the mortgage, interest, insurance and the amount that we believed would be sufficient for reserves.
All of us were professionals and none of us received compensation for our services. I did the legal documents. One of the other investors was a CPA. One had commercial property rehabilitation experience and she dealt with the contractors, etc. That part was agreed to upfront.
It worked really well. We paid our down payment. Paid our monthly payments each month. After about 8 months, we had our first renters in the first property and continued to make our monthly contributions. We deposited the rent and the contributions into the same account and after a few months, we had sufficient down payment to invest in a second property. We had a meeting of all of the shareholders and agreed (all but one investor who sold her unit to her sister for the payments she had paid in - so at no profit - but that was their agreement) to purchase a second property. Because we were rehabilitating commercial property, the rest of us believed that rehabilitating the property that needed it the worst that was close to the first property would be mutually beneficial. And we bought the second property and continued to make the monthly payments for another 8 months until we got the property ready to rent and it sat vacant, but ready for awhile. We got it rented it out eventually, but not for sufficient to pay the costs in full, so we continued to make monthly payments.
The original idea had been to contiue to buy property and rehabilitate it in the same commercial neighborhood until we had rehabilitated the whole neighborhood either by ourselves or that other investors got inspired.
The second building developed problems with the roof due to the age of the building that were not covered by insurance and were extremely expensive to repair. We basically got hit with a special assessment for the roof - an additional capitalization requirement in corporate speak. The roof damage caused our tenant to move out legitimately because it interfered with the business use of the property. So, we were out the money for the repairs and not receiving rent. So we continued to make monthly contributions. Eventually we got the roof repaired and got the property rented and continued to make payments to the capital account for a few more months. I made capitalization payments for almost three years before we could stop making contributions.
Eventually, the rents were enough to cover the expenses and to make capital reserves. After we had a lot of money in the reserve account, two units wanted to sell the buildings and cash out the reserves. The remaining investors (I was one of them) agreed to buy out those two units and own a 1/10th interest instead of a 1/12th interest. We had a professional appraiser appraise the value of the building and we figured out how much equity the corporation had (equity in the buildings plus the reserves) and used that as the value of the units. What we neglected to take into consideration was the investment risk. Oh, well.
The remaining 10 units, owned by a total of 8 investors, continued to participate in the original concept for a period of time that outlasted my first marriage (a total of 17 years, 11 years in the investment) and the period of my divorce (9 years). Shortly after my marriage to Ian, the original master mind of the concept died. Most of the other investors were well into their 70s and decided it was time to divest. We sold all of the properties (a total of 4 accumulated over the years) and split the proceeds. I recovered my initial investment and the capitalization payments that I had paid over the years. The profit was modest about 6K per investment unit. Not much, but only subject to capital gains tax.
I was glad that I had done it. We were able to get along throughout the entire process. I was the youngest of the investors at 29 when we started, and 50 when we divested. It was a great experience. It was mainly great because the women involved were all very congenial, dependable and smart. It worked great!
elaine