I still think it is a good area to invest in despite the increases in cost.  

I would recommend against being the GC unless you are confident of doing more than one effort.  

Additionally, what do you look for in a property to increase the value i.e. what are typical items to target?

Last year was back to earth; a glut of available properties drove the rates down for everyone and a drop in visitors also increased vacancies.

I self manage because no property management stuck out as any good. https://pr.mo.gov/boards/realestate/discipline/Paulakovich,%20Michelle.pdf

If you're a relatively new multifamily operator, you'll likely be required to hire a professional management company (inexperienced owners are typically not allowed to self manage the assets).

However, investing locally has become increasingly unfeasible and unrealistic due to the high costs.

For pros/cons of booking.com I would say the following...Pros:-if you use guesty you can sync your airbnb info into your booking.com listing info to ease the set up process-there are more options to check off in the amenities portion of the listing set up, so you can really display the uniqueness of your property-I would wager 90% of self-managing str hosts only list on up to VRBO/Airbnb, which means there are not nearly as many options for people to choose between, which means more exposure for your listing-rumor has it that booking.com just invested a large sum of money into building out their services to provide more vacation home listings rather than hotels.

Tell him it's time to do a remod and as a business you hope to market the place at a substantial increase.

However, because I believe it hurt bookings, I only charge the guests $230 and increased the daily rate to make up the difference, which has worked great.