I figure it probably won’t ever really be enough to get a great draw on once I retire, and my current plan is to roll it over and purchase real estate with it later on for cash flow.

I pre-paid 1 year's worth of home insurance as part of the closing cost even though I closed on the property in Jun 2021 (policy coverage runs from Jun 2021 to May 2022). 

Or you think I should just get the ball rolling and get preapproved with a conventional?

I'm allowing them to apply their pre-paid last month rent to the month of November.

The only thing I would suggest is ensure you can get pre-approved for a loan once the home is improved.

The difference should only be $25/mo if you roll that $12k in to the 5/1 loan. 

Now we have a couple projects rolling and just went under contract on a single family which will be developed into 8 units due to great zoning area.

You can always give the tenant the right to match your best offer, but be sure that they get pre-qualified for a home loan so you don't waste time with them if they can't qualify.

My lender just told me today that due to the fact that my father's business technically declared a slight loss in both 2019 and 2020, that he is unable to use any of the W2's from his business to qualify us for the pre-approval.

Once you have used your VA loan to house hack and still want to buy more rental properties, you could utilize a 10% down, no MI on a portfolio loan OOS in the mid to high 3s for a 1-4 unit property to get the ball rolling after your first house hack.