I am looking for insights if I should perform a DIY cost seg or if I should work with a firm? 

Licensed Real Estate Broker owns a Realty One Group Franchise and also owns a Property Management firm servicing Queens, Brooklyn, Bronx and Long Island

I am graduating from law school in May and will be practicing real estate law for a law firm in Philadelphia, serving mostly large commercial clients.  

James Funnel, Jr. with the firm Brody Wilkinson PC.

I do a lot of repairs and maintenance myself when I come down in the winter and during the quarters I make the trip, but here's just a sample of things I had to pay for in the last year:Pool screening: $985 (big hailstorm destroyed 13 screens)Irrigation repair: $394Irrigation repair #2: $230Palm trimming (twice: $200Pool light replacement: $950And all of that of course leaves out routine replacement of towels that get left at theme parks, sheets and pillowcases, busted blenders, and a host of other things I can't even think of right now. 

I would ask a PM in the local area who pays the taxes, sometimes the OTA's charge it to the guests but some places require the host to pay it.

Painfully clunky and outdated interface for both guests and especially hosts.

VRBO leaves payment to the host with API connection but Airbnb does not (or maybe you have a choice).  

But this can be off set because STRs can earn a lot more than LTRs.A host is very important to the experience of STR and responsiveness is critical.

There's going to be a learning curve but as you progress down the host road you'll learn what's needed to minimize your time needed on site.