I would focus on a few things:-What is the discount you are getting for dealing with the situation.  

We use Buildium, a property management software, where all applicants over 18 apply, undergo a screening process, and sign a lease.

That means you have to purchase 4166 records to use your $125, but Datazapp is even better than every other company because of you pay them $250 in advance they will let you make as many small purchases as you want during a 30-day period until you reach 6,000 records.The cost to purchases emails and phone numbers is much more expensive when you are using a customer list you own because of what I already explained, but if you don't have a list and you want information for property owners then you can limit your lists to only those that contain both email addresses and phone numbers.I think the reason most real estate investors don't do a lot of direct mail or bulk email is because it requires a lot of software and technical knowledge.

With that being said if you're using an esig software we are talking about a few clicks why not just do it the long way to be safe. 

I'd probably use local realtors to help re rent any vacancies and then possibly use a PM software like rent redi to keep everything in one place.Has anyone had management in place and then decided to opt out to self manage?

No more discounts.

After scouring the market, I was able to get large builder financing and discount incentives that allowed me to buy the property at below retail price and get good financing terms.

Banks and credit unions can also offer flexibility for investors that engage in strong relationship-building strategies, offering discounts and solid loans in exchange for borrowers willing to use the institution for other purposes (savings accounts, etc.).

Yes, definitely reach out to an accountant for help with an LLC, an IRS EIN, accounting software recommendations and tax planning. 

If the seller has already discounted the property considerably to justify the work needed, then you have to take that into consideration.If the seller is trying to sell the property full price needing repairs that’s a whole different story.