These condos cash flow about $500/month, so my friend lost out of $1,500 in cash flow, and paid $3,000 in carrying costs (HOA fees, PITI, etc.); so he paid $4,500 to save $2,000-3,000. 

Back of each home is against wooded area = not much backyard areas.Seller bought them back in 2014/15ish for $250k each, had all plans drafted and approved by HOA ($1500 each review!)

Although there is not a homeowner association in Oakwood, the city acts like an HOA with great attention to detail.

What are the maximum repercussions by the HOA or other entities? 

Yes the HOA fees and rules aren't ideal but if you find something that provides good cash flow is a good way to get your feet wet while you get experience..Typically with a Condo you're only responsible for the "Walls Within", landscaping anything outside the HOA covers it..FHA loan can work but if you're not looking to House Hack than its not an option..

I owned a condo and the mortgage with HOA dues on top of that came out to about $1,300/month.

Those typically rent around 1300-1400/mo and you can purchase them in decent neighborhoods like in Wake Forest for around 180k thus giving you the best cost / income ration you can get in current markets.Townhomes are great too and better for a lower starting cost, but you have to watch out for HOA, those can be pretty high.Not sure about driving for dollars, unless you have lots of time and enjoy driving a lot.

Also most HOA and uppity types like that have no problem with 30 or more stays) so the maintenance is all in house and the other stuff has to be handled by someone else. my goal is to be 90% hands off so I can be in the caribbean with my sister on a cruise and not have to worry.

@Jeremy Clendenin I would check and make sure there no outstanding liens on the property if there’s an HOA You’ll want to know that number or fee and if the HOA has a lien against the condo, Who knows maybe the previous owner didn’t like the HOA so he never paid his dues ?

Can the buyer of the condo purchase their own flood insurance policy in lieu of the HOA maintaining coverage?