With that being said, if you're comfortable with a long term hold, San Diego and especially coastal, will always be attractive imo. 

It’s better to have less rooms and to have them large enough to comfortably fit a queen bed.

Are you suggesting that being crammed in a small hotel room represents a better experience than being in a comfortable homey Airbnb?

Personal Circumstances: Consider your comfort level with debt and risk.

I pushed back on the idea of an up front transaction fee of 10K and told him that I'd be happy to pay a transaction fee at closing, but wouldn't feel comfortable paying 10K without it being tied to an acquisition.

Get out of your comfort zone.

You just have to be comfortable knowing that you shouldnt expect to see strong price appreciation unless you force through the NOI. 

In my experience, allowing these professionals to guide you can be highly beneficial, as they are likely to recommend properties they would be comfortable managing.

Your income needs to be 100x it and you need to invest 10% of your net(so less than $5mil) annually in structured product type investing incl RE, let it season for 3-5 years, re-invest the first bit of profits and by year 8-10 you should be comfortable.$500k annual income is alot for your average folk, but it's not "retire me" income at all.

Now to provide extra comfort and convenience to our buyers (who are mostly out of state) we agree to help them out by getting them set up with local property management that we work with closely as well as assisting management market the property for rent to place tenants.