Obviously there are some pretty major pros and cons with a tenant who has been their that long.

I work for a non-profit housing developer in Berkeley CA. 

The following IRS websites cover the UBIT rules. https://www.irs.gov/charities-non-profits/unrelated-business-income-tax To avoid UBIT it will be better if the self-directed IRA loans funds to the LLC as UBIT does not apply to notes.

I would then use the net rental profits from this home towards the down payment for a 2nd rental property (along with proceeds from any vacant land deals).  

You leave a lot of the profits on the table.

Either  1) you will get no loan whatsoever, or 2) It is some BS combination of "trade accounts" credit.....Office Depot, Home Depot, and other misc useless businesses......Not a cash line of credit.Once you qualify for any kind of business line of credit, there will be No upfront fee, and more importantly it will be because you have established an Actual ongoing business that shows a profit, and consistent revenues over a few years.Time to turn on your BS detector.

You want to make sure they're completely familiar with the entire process, because the underwriting is a major pain.

Your profits will also depend on your monthly mortgage payments.

Mostly rural , small hick towns, stlouis closest major city, carbindale marion two closest too me.

I assume major mechanical  updates.