Insurance claims are never fun and with being in an HOA certainly makes it a bit more complicated.  

However, especially for your first, I would suggest the money you pay for either option is a better value than doing it yourself.Pursuing an investment with a partner does complicate hings slightly and I'd recommend discussing the legalese with an attorney.How do you stop a tenant from wrecking your property? 

What attracts me about this approach is the ability of the investor to add meaningful equity through judicious deal selection and repairs, the leverage possibilities and the ability to put your capital to work over and over (high velocity). 

@Karen KushnerIn your two messages, you're basically asking to learn several highly complicated topics and then figure out how they apply to your specific situation.

Getting lots of LLCs is not always the sign of success, sometimes it is a sign of complication and it gets difficult to keep up with all the paperwork, so very well one could have slipped thru the cracks.#4  Now looking at all the success you have posted about the owner, they very well could fight if they loose it. 

Relying on general ideas is dangerous when it comes to taxes.Read this older thread to see why this area is far more complicated than you might think: https://www.biggerpockets.com/...

I invest locally and in a judicial state, which is more difficult to foreclose. 

Buying a house and renting it out is not that hard or complicated.

It is overly complicated, the service are terrible, and they often don't fix much of anything.

To complicate things further, you should have a policy around how and when they accept your offer.