Or all of these questions irrelevant, as long as rent is being paid and PM communicates great with me?

Many lost most or all of their money. 

You or a corporation you form or LLC you form can be the Managing Member of one or all the LLCs.

Or properties that needed all new roofs, or all new windows, or structural damage. 

Should I talk to brokers, browse Craigslist, search Loopnet, or all of the above?

The broker I talked to last week handles mostly high risk stuff with smaller insurance companies, it sounded like it was something most or all of his insurance companies would do as well.Kelly

Not sure if you are asking your question in a general nature or specific to a property you are interested in, but for smaller amounts such as that, it might be possible to get some owner financing, or all of it financed by the owner.

They are going to use the bank/loan officer we've gone through for every house so I've talked to him and he agreed to let us finance some or all of the downpayment if needed.

Then rent out the other 3, or all 4 units and continue living in an apartment until you build up your savings.

He is adding 8 support beams to each building since there is inadequate support for the buidlings and the floors are uneven.We wrote the contract up based on him using 18", one foot diameter concrete footings placed into the dirt floor.