I do recommend house hacking to those just starting off real estate investing. 

Bad reputation with some agents- We've had a number of agents recommend to their clients to reject a NACA offer.

I wouldn’t recommend it, but I would never want the stress of an uncomfortable mortgage payment.

We actually challenge our clients to diversify their RE portfolios amongst Class A, B and C (We do NOT recommend D!).

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

You will want the full set of plans: elevations, electrical, mechanical, plumbing, floor plan with signatures and seals.For the mini split, some recommendations: If you're going to use 2 heads (one for living room, one for bedroom), get 2 separate single zone outdoor units (not a multi-zone).

Rent Roll13. property survey14. prelim title report (your broker can help with that)I DO NOT Ask or recommend my clients ask for tax returns, credit reports, bank statements - These fall into financial privacy protections and if my buyer walks from the deal, there is too much liability & risk with having that information if were to be leaked.If a third party management company has been managing it, you'll get basic information (income/expense, rent roll & leases, maintenance records, capex (maybe if they oversaw)).Owner operated properties will have less of this information as most mom/pop operators don't keep good records, in my experience.Don't worry about all this BEFORE the offer. 

Material participation might involve managing properties, handling leases, or overseeing maintenance—activities that are more hands-on than those of a typical passive investor.I recommend doing some tax planning and see what options you have .

judgment is higher than $5k who do you recommend for #2, or #3 option?

I do recommend a cap and you can also have thermostats with upper and lower limits so one person can't set it to 80,  put those limits in the lease.