I'm looking for something that can handle the financials, track maintenance requests and payments, and deal with communication (announcements, message board, etc.)

The zoning key words you will want to look for are "Accessory Dwelling" or "Principal Building".

That is all I know, I know that if I did want to take it as a career then advertisement is key.

As someone who started investing turnkey 6 years ago, one key to successful turnkey investing is to be sure to vet the company thoroughly, and I think that should include a visit to the market to meet with those you are considering, see their rehab work, the neighborhoods they investing in, and learn about the quality of their property management.   

Will come down to the HOA board and the communications had with them.

Well, maybe a shortcut to getting you info that might help you... what would be your vision for getting 'more involved'?

The key to forecasting a downturn is when you start seeing a few cities start to head south.

If so, it would be a good precaution to re-key.

Sounds like you would be better off going the turn key route.

Shop around for utilities if you are paying for it.Shop around for dumpsters line up the contractors to do all maintenance requests or upgrades you need to do.get ready to Install motion lights outside prepare ownership change letters to tenantscopies of keys copies of all leases (should have got in DD)Ask the lender and title company to provide you with the final Settlement statement so you see which other costs to expect.