The proceeds from the flips will be re-invested in syndication deals or move back to invest in stock market.

That works fine for stocks - which aren't 'needy'... and maybe having a few properties that would be ok.  

Not counting maintaining the LLC. 

It's definitely a frustrating part of the business, especially when you're trying to maintain cash flow and unexpected repair costs pop up.One thing I've learned is that some of the more real estate investor-focused insurance companies tend to be a bit more lenient on inspections or are more upfront about their requirements before binding the policy.

Limited appreciation, old housing stock in need of major capex, population decline in many markets...Can you pick a market that's a couple hours away so the price point is lower, but you can be in-person and hands-on?

Compared to the stock market, real estate investing offers better return on investment and lower risk.

@Khayla WilliamsI strongly recommend against borrowing 100% for a propertyThere is significant risk in owning real estate including section 8 and maintaining the home in a certain condition and if you do t have the funds for those repairs you could lose it all.I always recommend people budget and save enough for a down payment and reserves before getting into their first property.

I would think if association is responsible for maintaining roof and it caused the damage, then they’d be responsible unless docs state otherwise.

But, thank you for chiming in, and you're right, hopefully we all love RE and the stock market. 

Stock market returns estimated to be much lower next 10 years.