If you are newer I'd suggest a house hack unless you can rinse/repeat this process again. 

@Marcus Stokescan you start with a live-in flip or house hack instead?

Security Deposit: 2600Lease states no smoking/painting walls/no hanging things on wallsTenants have moved out and have left two truck loads of garbage to be removed.Damaged doorPainted walls which got on the ceiling and trim Lots of holes on the walls throughout the houseDamage from windows being left open constantly Weed was clearly smoked in the house (smell throughout the place) so we need to deep cleanWater bill wasn't paid so I had to turn back on utilityMissing keyQuoted costs:$450 junk removal (some furniture)$935 for damaged doors/windows, painting cleaning$30 for utility turn onTenants were only there for a year before moving out so a lot of this is beyond normal wear and tear. 

Additionally, the house is 25 years old and could use cosmetic updates to increase rental appeal.

Most traditional property managers don’t handle this setup due to challenges like managing tenant disputes, coordinating overlapping move-ins/outs, and the risk of Fair Housing violations when selecting tenants.

@Pat Aboukhaled I would ULS (unit lot segment) the primary house and include a clause in the call option that would prevent them acquiring the DADU.

That's exorbitant in my area for a house that size.

House Hacking using the VA loan to live on one side while renting the other is great.2.

i also had HVAC mystery issues in my first duplex when we house hacked it.Regarding the Daikin Mini Split - I have one in the 3rd story of my current home and it seems to work great for us. 

I am not even sure if the villages offers this type of real estate in which we could “house hack”.