In my market, I only have one vendor qualified for appliance warranty work, and the warranty companies paid him half his standard fee for each service call. 

- Loss of historical data (for both IRS audits and for personal portfolio tracking.)You should be able to print the general ledger and Balance sheet / income statement for each period.

Your IRA can borrow, but you have to be careful to not personally guarantee it.

I am wondering if transferring the cash periodically to a standard brokerage IRA account may be my best option.

It depends on who you're hiring but that seems fairly standard.  

Quote from @Michael Smythe: @Jerry NoguerasRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

However, you can get loans that are based on the performance of the rental and not your personal income and debt.

Personally I would not take a negative cash flow deal.

As we all know, the standard way BP says to calculate cash flow actually leads investors away form long-term opportunity and leaves a lot of investors on the sidelines because they don't understand IRR and the multi layered dynamics of investing long-term.  

I personally think being a landlord in Chicago is easy and I have never had an eviction.