Ultimately, the best approach depends on factors like the size and complexity of your operation, your comfort level with HR tasks, and the services offered by the property management company.

I see that most/all lenders include vacancy in their calculation, whereas the other two expenses are sometimes included - depends on the lender.

There's no one-size-fits-all answer, it ultimately depends on your individual circumstances.

Depends on the property. 

I think it all depends on what you want your reputation to be.

WHERE in the Orlando/Disney market will depend on your lifestyle preferences.

But can vary depending on your syndication structure/filing.A good attorney will be able to steer you in the right direction with this.That being said, these questions always make me wonder.

This may be a barrier depending on the municpality and even if not, once you weigh the time and costs associated with the added overhead you have to determine whether self performing is worth it.

Customarily an insurance carrier will provide legal representation for negligence but depending on the fact pattern may not even pay for damages.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23DSCR lenders generally let you vest either individually or as an LLC.