Self Managing is always an option but with City inspections involved at every turnover, I am not sure how feasible it is to manage remotely.

What I do is include an option for property owners to opt out of the self serve showing in their management agreement. 

You have a number of options, it just sounds like you need someone competent to explain them to you.

Additionally, how long does it typically take to convert the units from free-market to Section 8?

Some companies hand-scrub your lists to find the best contact information.Utilize a company that has flexible pricing options and non high volume minimums to meet your needs.

Hello Nicholas, there are a few drawbacks: -Complexity and Scrutiny: This approach could attract scrutiny from the IRS, as it's not a typical way to manage rental properties.

Our only other option would have likely been a bridge loan for this size of property. 

First year and beyond is typical on a schedule E, same as a LTR unless your providing substantial services.

Is this a reasonable expectation and a good option?

Negatives to VA Loans- Seller pays for termite Inspection-Termite damage needs to be repaired- VA property condition requirements- Longer close times- VA borrowers are typically, but not always, First Time Home Buyers, so all the perils that go along with that.- VA Borrowers very often tends toward very subpar lenders like USAA for instance.