Regardless of whether or not having a short term rental in your small complex could help or hurt property values and your ability to convince the HOA of the former, please think about the viability of your STR if the neighborhood sentiment is anti-STR.

NO chance HML is going to do this deal.. they don't do 100% Loan to cost second liens ESPECIALLY  in IL were the foreclosures are long and expensive.AS @Josh Auxier  alluded to make sure your state does not have anti equity stripping laws.

Ibrahim, I see the decision as pro-investors, not anti-investors.

Their are multiple tradeoffs for each positions, but the big ones are: Anti Registration: The rental stock will be more prone to having dangerous code violations, which in turn, on average will increase the rate of injury and death.

This is not only for securitization, but there are also Anti-Money Laundering laws that we must adhere to. 

Feds are anti-coal now so they won't support that.

If you can keep inflammation down in the body (keep hydrated, use anti-inflammation spices like turmeric, limit sugar intake, don't eat late at night so you can intermittent fast) you'll be healthier, will manage stress better and when your body doesn't feel sluggish I believe sadness and depression have less of a chance of showing up. 

Your faucets are not to current code, as they are not "anti-scald", so changing them and adding a shower riser would be a minimal approach, but doable.

Then you are going to get the anti turnkey people, then you will get the pro turnkey, etc.  

My advice is to stick to investing in true vacation rental markets like Gatlinburg, Panama City Beach, Big Bear, and several others to ensure the smallest chance of anti-STR regulations being imposed in the future.