I would like to ensure that my future "investment LLC" falls into my trust (either by direct ownership of the LLC, or transfer on death) when I die, so that it can skip probate.It seems like having an entity to aggregate a number of deals would simplify everything a bit (at least from an estate planning standpoint), but maybe it would complicated taxes so much that it's not worth it.Thanks for any advice!

I dont think thats over simplifying, but the logic here under current market conditions means prices will continue to go up.

In my example, it would be leaving the old $200k loan in place and getting another $50k equity loan.The rules are a little trickier than my simplified example, but I hope it gives you an idea.

Some landlords will collect security and first month at signing to simplify the process (maybe last month too). 

I just want to simplify my record keeping and don't want to keep track of every little expense.

My reasoning is it simplifies research, allows me to use one manager that hopefully is good (may take some trial and error), and may allow for an occasional checkup trip (these would be fairly rare though).Anyone else buy remotely?

For purposes of simplifying, I will use round numbers.I have a seller (family member) looking for $100,000 for his property.

To simplify it, have multiple resources for leads.

How this is going to work is (simplified):Rental income( rental Expense) ( depreciation) Rental Income/Loss - ( This is your passive income or loss) If income: The rental income is taxed as ordinary income that will be added on top of your W-2 income (W-2 is non passive income). 

If you have the cash in your plan, skipping the non-recourse financing certainly simplifies things.