Make sure that your listing has pictures (the more professional looking, the better) and a great description.

The upsides is that your property is professionally cleaned after every checkout, upkeep is super important as this is a business for him and broken or damaged listings don’t do well at all.

If all your questions are answered positively, I would still have a contingency clause in the purchase agreement that would allow you to "walk away" without any penalty that is financial and before I closed I would hire a professional and experienced Inspector that would make you aware of any possible negative/unexpected things that he discovered.I would not buy a single family house for rental unless it was used as a "house hacking" loan that I felt pretty good about qualifying for it.There is only a couple reasons that could make it OK to purchase. 

Once again start talking to a realtor ahead of time to open your options up and start to get an idea of the market.I highly suggest you look for a realtor with the Military Relocation Professional (MRP) designation because they have taken extra courses to learn more about service members and more importantly the VA loan.

These are professionals with additional training and a stricter code of ethics.

https://www.narpm.org/find/property-managersThese are more professional and educated PM's with higher standards of Ethics

the lady I talked to said it counts against you when you do something like going from an IT professional to say something like auto mechanic because you're changing fields.

., professionals who are in the area for a year for work and want a large space to rent for that period.

Went to college for architecture and have worked in my professional life as a building inspector, insurance underwriter, and actuary, and I lived in a 2-fam and had two more 2-fams in my hometown of Buffalo, NY, and sold those when I got a job offer and moved to New Orleans, LA. 

Readers are advised to seek professional advice.