I'm working with a client who's interested in a home that's currently used as an airbnb. 

I work for corporate America and looking for an exit strategy as I enter my mid 50s. 

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Additionally, how should I work with my insurance company/police/contractors to prepare for the worst?

These are electric only systems - dont work well in older buildings - but newer construction they should be great.

Another thing is getting multiple bids on the work. 145K and 200K is a big difference.

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.

Can try to reposition to Class B, but neighborhood may impede these efforts.Vacancy Est: Historically 10%, but 15-20% should be used to also cover tenant nonpayment, eviction costs & damages.Tenant Pool: majority will have FICO scores of 560-620 (approaching 22% probability of default), many blemishes, but should have no evictions in last 2 years.

Set the price high and let the market determine the rent, by lowering it if there is little to no interest.

Quote from @James Harryton: Hey, I recently bought my first rental property in Polk County it doesn’t cash flow enough for me to have a property manager so I would have to manage this myself for the time being, however in about 6 months I would want to get a HELOC on the property and use that as a down payment on maybe a multi family and then rinse and repeat, I was wondering if this sounds reasonable or would I have to do something else, and also because the market value of homes are so expensive around me, the 1% rule for rents don’t really work for me thank you so much