Hi Stan, glad to have you as part of this community! 

I am wondering if I can claim it as a repair(counting against rental income) or if it must be claimed as an asset (with depreciation benefits)?  

Naturally your property must sell before you can take title to the new one, but nothing prevents you from getting it under contract and make the process as smooth as possible.  

I'm on the hunt for real estate meetups to expand my experience and network, but I must not be looking in the right places.

One very powerful tool is the built in analytics and graphs that Vrbo has.

I know its mean to say that people who do their own contracts get what they deserve, but you must know that if you are paying a couple hundred thousand dollars for something it just might have been worth spending $600 on a lawyer to do a proper contract for you.

Now that I have answered your question, I'd like to share my questions and possible concerns. 

We have previously tracked all expenses manually in google sheets and produced financials statements manually, also in google sheets.  

The 10% to 18% cost of the DST would be repeated every time the DST terminates and a new 1031 exchange must be made into a new DST, maybe every 5 to 8 years, whereas the capital gains tax would be a one time cost.

I used to be in finance and they'd have scripts for interactions like that as newbies but I would say just try to be yourself.