Quote from @Sean Gallagher: This is my fear, I have not crossed over to a property manager but just what you discuss has me worried because one day I know I'll have to. 

He worried the upscale kitchen appliances and designer finishes were too much for the area.

Purchase price: $187,000 Cash invested: $15,000 Sale price: $259,000 I got tired of moving place to place and worrying about finding roommate, security deposits and not having enough money to deal with maintaining someone elses home.

I like umbrella because there is no worry of being pierced for inadequate separation of finances, if sued you have a heavy weight in your corner who has all the consequences of a defeat, and because usually it is reasonably priced (mine today is not so reasonably priced but I believe it is mostly related to the risks of CA).I do understand that the probability of needing the umbrella policy is low.  

I would recommend getting a free cost/benefit analysis to see if you specifically could benefit from the study.Real Estate Professional Status

Purchase price: $187,000 Cash invested: $15,000 Sale price: $259,000 I got tired of moving place to place and worrying about finding roommate, security deposits and not having enough money to deal with maintaining someone elses home.

Knowing your long-term plans can help you build a long-term financing strategy so that you are not just worried about purchase number 4, but also purchases 5 - 20+ (if you plan to continue to invest).I'm an investor and licensed mortgage broker.

No worries if not, just thought about you.

He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

That also made me hesitant about Cashiers, meaning I worried that the mindset would spill over.