I've ran into people that have that attitude of, "Oh, I could be a landlord, it can't be that hard."

Great attitude! 

Send him a written signed offer with a high EM deposit to help sway his attitude.

If a newbie is willing to bring their A game, a can do attitude, a reason for someone with experience to JV with them (money) and a willingness to follow then there should be success.  

Keep up your attitude.

When no one attends meetings, Boards often take the attitude that it is "their" HOA and they can do whatever they want.

.- Self-starter with entrepreneurial mindset, positive attitude, with a knack for creative problem-solving- Excellent client service skills gained through daily communication with ultra-high net worth ($10M+) clients - Detail-oriented individual with precise execution, facilitated many high-value transactions such as wires, trades, etc that leave no room for error- Fantastic with numbers- Deep understanding of investment vehicles and financial markets, including the real estate market and how various factors such as interest/mortgage rates and inflation impact supply and demand- Massachusetts real estate agent license- Graduated from Tufts University with a 3.9 GPA- Native English, conversational Japanese and Spanish, currently working towards business-level Japanese- References available upon request Even if you can't use my help, I would be grateful to network with any investors/aspiring investors in the Bay Area, so I thank you in advance for interacting with my post!

What's your general attitude about it?

Given the circumstances of the renter during the repair period the $300 seems like a good business decision = (not charging rent during a time when the unit is non-operable as a legal rental).If they did not have the option of staying with a relative (not everyone can--new to the area, etc...) then the closest Motel seems like a reasonable offer.I think it comes down to the rental experience that you want to (or need to) offer the renter (in your market for that property class) to hopefully retain them long term (excessive turns are a money eater).Some areas and some renters are way more self sufficient than others who are used to having everything in life handed to them.Self reliant Wyoming-ens might have a different attitude (or needs) than some of the more urban renters, hence the different (profitable there) business practices (which reminds me of this song)... https://www.youtube.com/watch?

If you're bringing value to people and you have a humble, eager to learn attitude (which it seems like you do) people will naturally be drawn to you and want to help you.