Insurance would cover it, I would pay the deductible, and no assets would be lost.If you are in an area like San Diego where people are more likely to sue, a judge is more likely to find you guilty, and the payout is expected to be higher, you may consider an umbrella insurance policy.

Lots of people who have trailers don't own the property they are on and sell them.As for the owner of the land expecting tenants to do repairs-there shouldn't be many repairs required to the land, just the trailer that is on it (which your grandmother owns and should be responsible for maintaining). 

People house hacking have far different expectations than someone buying properties with cash. 

It wasn’t a massive deal—our expected assignment fee was $10,000—but when you’re growing a business, every opportunity matters.Everything seemed to be moving smoothly until the title search revealed a major roadblock: the mortgage discharge couldn’t be cleared because the person who needed to sign off was deceased.

@Tove Fox hope you find this copy & paste useful:)-------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Trustin your PM partner is important and they will follow your lead, so don't expect them to provide you with your business plan. 

What are you expecting from this post? 

I did file a large claim a few years ago for a broken HVAC.

Look for books published in the last 2 years as some of the books post 2010 seem to give people unrealistic expectations.

@Rafael Valdor some advice when screening PMCs-----------------------------------------------------------------------------------------------------Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.