I'm looking for a great local photographer to take photos of my STR.

Judging from this photo it looks like no permits were pulled from few things I am noticing with the work so I would for sure check with town to verify.

Many property owners like the stability that comes from having a good tenant that they know, so if this is more important to you, then it may make sense to keep the existing tenant and give them a nominal increase.For me personally, I believe in running all properties like a business, so if I have the opportunity to get a significantly higher rent with a qualified tenant, then I'm going to take it. 

No point in shopping around for rates unless you have an accepted offer.All your income and bank statements should be labelled in pdf files on your laptop or desktop not photos on your phone.

Reduce yearly dues to a nominal amount, etc.

Watermarked photos help.

Are their listings detailed with good quality photos?

Ask the agent for the Rent Roll, T12 (trailing 12 months of expenditures and income), copies of the leases and estoppel certificates, current photos and video and make your offer subject to an inspection report (the bank will add another filter by ordering an appraisal). 

If you want to see how it looks, here is a link to my drive with all the photos.

It had bad photos and appeared to have incorrect square footages, but I knew the neighborhood and decided to check it out anyway.