We avoid HOA neighborhoods for our properties.Happy to discuss more specifics of our approach there if helpful.

Does anyone have any recommendations for a real estate agent that has experience with VA Loans (specifically- assumable VA loans)?

Depends on what your buying criteria is - budget, ROI, neighborhood class, etc all need to be considered.

Maybe Crexi or a specific skip trace tool? 

I've got some insights on areas that fit your criteria.

I clarified by asking if it needed to be 14 days, 10% of booked days, any specific number, etc, she said no.

If you can meet with a real estate specific tax professional and discuss your tax strategy at the beginning of the year I think this would be worth the fee.  

I know how important a real estate specific accountant is especially as I start out, but after a couple years of working with a professional and if no significant changes have taken place and I only have 1 investment property, could I not do the taxes myself?

But, that is not always the right answer and you should speak with someone familiar with your personal situation to get advice specific to you.

I don't know all the specifics of the deal you're in, but my gut reaction is that if you're taking this risk, you need to get paid, either in the form of interest or a higher price.