@Marcus Palm If you are going to pursue a passive investment through syndication, make sure to analyze the opportunity through the new "Covid Resistant" lens we should be wearing. 

lol  But seems like you know what has to be done (20+ years on a regular shingle roof is good), so find a reliable roofing contractor in your area, work out a deal and get it done in about 1 month (weather permitting), and things fall in place.If you have specific Roofing questions, let me know!

Pretty much every city in the U.S. has some kind of weather issue.

If you were going to get some resistance from your HOA, it's likely be around short term renting.

Hedging bets and building in risk mitigating plans/processes can generally get one through a rough patch or two.If a deal can't weather an average storm, maybe one should not set sail on that type deal.

Even with a downturn because of principal paydown the asset has strong capability to weather multiple market environments.

Typically in my area it depends weather you’re on pump/septic system in which case it’s on the property owner.  

Coming from finance, the path of least resistance for you would probably be the lending world: underwriting, becoming a mortgage broker, etc.

But if you do decide to go full time - make sure to put a little savings aside  ( about 3 months) to help weather the slow periods. 

Also you can add fire resistant insulation even if the town doesn't require it.