I am super happy for you and even more impressed with everything you did to get there.

I had hand selected the tenant for it and he was terrific.

This can help you set up a connection much quicker and gives you an opportunity to make a personal first impression that you dont get with email/messages. 

There are lots of options to meet, I think it all comes down to how many people are planning on showing up. if we have 20 people coming then we may want to find a better place than Timmys or Starbucks but that's just my impressions.

I have a lot of experience and can tell you that the majority of renters ask to sign a longer lease because they want to distract you from looking too deeply into their past, they want to entice you to select them over other qualified renters, or they want to negotiate a lower price.

San Diego recently implemented an STR quota and one of our STRs was not selected in the lottery. 

D. (2) states "if third-party payments received exceed Buyer's obligation, the excess amount shall be paid to Broker, or credited to Buyer, or __" with the buyer's agent selecting if excess above the agreed payment amount shall go to the broker, buyer, or someone else. meaning that the buyer could receive the excess if the commission offered is higher than that agreed to between the buyer and their agent.

Looks like many people are mentioning Crexi and Loopnet but my impression was that good deals get picked up before reaching those forums and the best way to get a good deal is via an agent active in your target market.

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You won't learn a ton, but you will have skin in the game, and you will see how the business actually works.If not, then you need to learn the business before selecting markets from afar.