Can a Hard Money lender also take care of the upfront costs for a rental? 

From the tenant's pov, I don't see why a conventional lender would have issues with a tenant buying the property as a primary that they've been living in.Cheers!

I'll take having a health care directive over 10 LLC's any day.  

Whatever you all do, please be careful. 

Granted that's apples and oranges, because the new homes are larger and all in the suburbs, but as long as you can buy an existing home for half the price per square foot than a new construction home I would be careful with expecting peak appreciation.

In the next 1-5 years you could have some serious cashflow - why would you care about the associated taxes?

Lawn Care: Regular upkeep, normally the tenant's job on single family residences stated in the lease.7.

I don't care if they bring in a couple kids, just wasn't sure how to handle it. 

Donate the Property: Donating the property to a qualified charitable organization can provide you with a charitable deduction equal to the property’s fair market value and eliminate capital gains taxes.Implementing these strategies requires careful planning and consideration of your specific financial situation.

Any time you use a HELOC, you only want to use 50 percent of the available equity or less so if you can do that over time carefully, it will work.