Most experienced investors are on here too so feel free to post topics, being specific really helps to detailed answers.

I've now used my VA loan several times to "house hack" in some pretty rough markets, more specifically California.

There's some finer details in MLS, but not needed unless you were deep diving a specific property and by then it'd likely be to where you're trying to get it under contract.... which would mean you'd have a agent.

Specifically looking for gutter cleaners, exterior painters and plumbers. 

Also, if you have a specific number in mind, just wait and see what they provide you from an appraisal and then negotiate.

If you have any specific questions let me know.

That depends on state law, so it's a state specific issue.One thing they can probably do is fine the homeowner lots of bucks and make it cost prohibitive for the homeowner to rent to Airbnb.Then they can put a lien on the property and when they go to sell it, have fun negotiating with the HOA.

I'm looking to diversity out of CA real estate market into mid-west / south / south-east and am looking at Indy specifically.

My first suggestion is to really sit down to think out your goals and be specific.

I would suggest you add an addendum to the lease that notes the specific things you will  be paying for and have tenant sign as well as yourself.