I am buying a Short term rental this year but will be using a property management company only for this year, which prohibits me from claiming bonus depreciation. 

Using a rental is one of the best reasons to buy one so I like your thinking there.The proliferation of STR in ski areas have made areas a little farther out more of an option in some of the ski areas so you can track the options by looking where they short-terms stop on the map in the areas you like.

Sure, you can track everything just using a spreadsheet or you can use the "shoe box" method for your receipts (I've done both!)

Plus, the product itself is 17 years old, which is eons in the software field, so it's nice to not be using a startup.Unfortunately I signed up for the free trial and then didn't take notes, and now that I am getting around to the review the features are mostly shut off for me since I canceled several months ago to avoid paying.

If you’re not using a PM (I’d suggest getting one.) then I wonder if there aren’t business that specialize in moving out tenants.

Would i be able to avoid capital gains by selling it, then using  a 1031 exchange to buy a multi family unit that i plan to also occupy?

Are you using a PM, you can automate or become your own PM for a while,  Are you charging a premium (additional $50) for being on a month to month lease instead of standard year lease. 

If you don't want to have to cut/rotate the keys (by using a rekey lock/tool) then I'd opt for the smart lock hands down.

Also, by using a DSCR loans, investors can leverage their capital to purchase multiple properties, which could potentially accelerate their investment growth and overall financial returns. 

If you are using a local credit union or balance sheet lender they have additional qualification standards but I see you are in Oxnard.