These reasons make me think that you need to be at the forefront of someone's mind by doing direct mailing, contacting agents, lenders contractors, (whomever) frequently and reminding people of your specific buying criteria and other such strategies as a method for landing deals with less competition.

. :) I've attended a few events on Meetup but they only happen once a month so looking for something more frequent.

Sure, you can hire management but they will indeed take 20-30% of revenue - at that point you will likely still have more income vs LTRs, but is it worth it to have constant strain on your property from people constantly coming and going and small repairs popping up frequently.

How frequently should I increase rent assuming that the $1400 a month is fair?

However, I have read that these rentals may bring in less revenue although easier to manage due to less frequent turnover.

Additional liability, maintenance, frequent painting, rust etc.

One of the things I have started doing is looking for the types of chain restaurants that my ideal tenant will want to frequent as they will have already done the market research for me.

And if they start to rise, that frequently creates more demand as people who have been thinking about buying decide "It's now or never." 

Although those type of phone calls don't happen frequently, I think it's important to be aware of it upfront. 

So expect more frequent and high unforeseen costs coming your way.