Those that own it can be harder to sell as the cash flow from the business will cover the debt service for the business, but not for the real estate.Example: I had a very high-end assisted living facility on the market. 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

If the water bill is $100 a month, increase the price by 20% (or whatever you decide is fair) to compensate you for the time required to split and bill and to cover additional use when tenants squander the utility.

@Michael Fucillo haven't played with RentVine also.Would recommend Buildium for what you need as it covers all the basics.Everything else is more geared to managing for others.

The general idea is that you must acquire an interest in real property you do not already own, and since you already own the subject real property you want to build on, the transaction must be structured so that you are creating an interest in real property you do not already own (in fact, it does not yet exist).

There are short-term rental management companies that can help with that.One that I work with in Michigan covers the entire state and can advise on local short-term rental regulations or regulations that may be on the way, they can give you an analysis of the demand for short-term rentals in that area, nightly rates in that area, monthly occupancy percentage, and projected monthly income.They also let you choose the level of service you would like from them from full service to minimal.To your success!

I would recommend leveraging the BP forums to connect with existing syndicators.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

I transitioned out of existing inventory and things like worse markets there wasn't enough capital drivers or growth to make the numbers work. 

Because you are essentially buying into an existing business, the sale of it could generate a disproportionate amount of tax for you given your time in this deal.